Senate Democrats on Tuesday delivered a stinging blow to President Obama’s trade agenda by voting to prevent the chamber from tackling fast-track legislation.

A motion to cut off a filibuster and proceed to the trade bill fell short of the 60-vote hurdle, failing 52-45. Sen. Tom Carper (Del.) was the only Democrat to back it.

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The vote is an embarrassing loss for Obama and senior officials in his administration, who have spent weeks lobbying Democrats intensively to support fast-track. The bill has an unusual coalition of backers that notably includes Obama and Senate Majority Leader Mitch McConnell Addison (Mitch) Mitchell McConnellMomentum growing among Republicans for Supreme Court vote before Election Day Trump expects to nominate woman to replace Ginsburg next week Video of Lindsey Graham arguing against nominating a Supreme Court justice in an election year goes viral MORE (R-Ky.), who are longtime rivals.

Fast-track has run into significant Democratic opposition led by Senate Minority Leader Harry Reid (D-Nev.) and Sen. Elizabeth Warren (D-Mass.). The legislation faces even stronger opposition from Democrats in the House, and the surprise Senate failure could signal the beginning of the end for one of Obama’s top priorities.

Obama last week invited a group of wavering Democratic senators to the White House, and Vice President Biden placed calls to swing votes. The charm offensive showed little effect, however, and Republicans excoriated the president for failing to move members of his own party.

“Essentially what the Democrats are doing today by trying to block us from even getting on this legislation is throwing their own president under the bus,” said Senate Republican Conference Chairman John Thune (S.D.).

The vote is a big win for Reid, a staunch opponent of fast-track who appeared to have little leverage after the trade bill passed the Finance Committee with a bipartisan 20-6 vote.

“The simple fact is that to pass the Senate, bills must have strong Democratic support,” he said in a statement after the vote. “Sen. McConnell needs to work with Democrats for our votes. I hope he will reconsider his approach.”

Labor unions and other left-leaning groups declared war on the fast-track bill, which they argue would ship jobs overseas. The Senate is generally a more pro-trade body than the House, making it easier to move trade agreements through the upper chamber.

Obama has shown irritation at the barbs thrown at him by his own party — and returned fire. He has repeatedly said Warren is “wrong” on trade in recent interviews. Sen. Sherrod Brown (D-Ohio) reportedly said Tuesday that the president went too far, suggesting the comments were disrespectful and possibly sexist. Obama referred to Warren by her first name in a recent interview with Yahoo News.

Terry O’Neill, president of the National Organization for Women, went even further in an interview with The Hill on Tuesday.

“Yes, I think it is sexist. I think the president was trying to build up his own trustworthiness on this issue by convincing us that Sen. Warren’s concerns are not to be taken seriously. But he did it in a sexist way, saying, ‘The truth of the matter is, Elizabeth is a politician like everybody else.’ … I think it was disrespectful.”

Meanwhile, Reid managed to unify his caucus against starting debate on the trade package by shifting the debate into an argument over procedure.

“We’ve been very clear for a long time that the bills that came out of the Senate Finance Committee by a big, big margin should be put together and put on the Senate floor,” Reid told reporters shortly before the vote.

Senate Democrats demanded that McConnell combine the fast-track bill with three other pieces of trade legislation, including a customs bill that would address currency manipulation.

Tuesday’s opposition included Senate Finance Committee ranking member Ron Wyden Ronald (Ron) Lee WydenGOP senator blocks Schumer resolution aimed at Biden probe as tensions run high Republican Senators raise concerns over Oracle-TikTok deal Hillicon Valley: TikTok, Oracle seek Trump's approval as clock winds down | Hackers arrested for allegedly defacing U.S. websites after death of Iranian general | 400K people register to vote on Snapchat MORE (Ore.) and other Democrats who back the fast-track bill.

“The group is concerned about the lack of a commitment to trade enforcement, which is specifically the customs bill,” Wyden told reporters in explaining his opposition.

McConnell has offered to bring to the floor a package combining fast-track, which is also known as trade promotion authority (TPA), and the Trade Adjustment Assistance (TAA) program, which helps workers displaced by foreign competition.

But he refused to combine those bills with the customs and enforcement act, and the package of trade preferences for sub-Saharan Africa.

“Until there is a path to get all four bills passed ... we will, certainly most of us, have to vote no,” Wyden said after meeting with a group of pro-trade Democrats.

Wyden was joined by Democratic Sens. Michael Bennet (Colo.), Maria Cantwell (Wash.), Dianne Feinstein (Calif.), Claire McCaskill (Mo.), Patty Murray (Wash.), Bill Nelson (Fla.) and Mark Warner (Va.).

Republicans accused Wyden of breaking a deal they say he struck with Senate Finance Committee Chairman Orrin Hatch (R-Utah) last month to move only TPA and TAA in tandem.

“The ranking member of the Finance Committee has changed the understanding he that he had with our chairman,” McConnell told reporters.

Another winner is Brown, a liberal Democrat and vocal skeptic of free trade. He lobbied his colleagues for weeks to insist on combining all four bills into one package.

“Sen. Brown brought it up to me right away, that he thought keeping them as a package was critical, and he worked the caucus on it,” Senate Democratic Whip Dick Durbin (Ill.) said.

The White House downplayed the defeat, with press secretary Josh Earnest chalking it up to procedure.

“It is not unprecedented for the U.S. Senate to encounter procedural snafus,” he said. “We’re going to continue to work through these challenges.”

Earnest dismissed the notion that the vote is a sign the president’s aggressive sales pitch to Democrats on trade fell flat.

“I would urge you to withhold judgment about the president’s persuasion ability ... until we’ve had a chance to advance this legislation,” Earnest said.

Hatch and Wyden tried to hash out a last-minute agreement to allow the trade package to come to the floor but were unsuccessful. Hatch said he would urge McConnell to pull the trade package from the floor if Democrats block it.

The bill could return in the next two weeks, but Tuesday’s setback means it will be very difficult to pass trade legislation before Congress’s Memorial Day recess.

McConnell declined Tuesday afternoon to reveal his next step.

He suffered a setback along with Obama, because he wanted to pass fast-track this month to give it maximum momentum heading to the House.

But the failed vote gives McConnell the chance to highlight divisions in the Democratic Party and portray Senate Democrats, who are aiming to win back the majority next year, as obstructionists.

“Blocking the Senate from even debating such an important issue is not the answer. Senators who do so are choosing to stand with special interests and against the American jobs that knocking down more unfair trade barriers could support,” he said in a statement.

Two Republican presidential candidates, Sens. Ted Cruz (Texas) and Rand Paul (Ky.), voted in favor of taking up the trade bill.

Another, Sen. Marco Rubio (R-Fla.), missed the vote, as did Sen. Lindsey Graham (R-S.C.), who is considering a White House run.

McConnell switched his vote from yes to no, which allows him to return to the measure at a later date.

Kevin Cirilli contributed.

Updated at 8:43 p.m.