Pivaloyl chloride → HCID 67585187, compound

HRID 727653Notes

Reaction equation

HRID 727653 reaction equation
[CH3:1][O:2][C:3]1[CH:31]=[CH:30][C:6]([CH2:7][S:8][C@@H:9]2[CH2:13][N:12]([C:14]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=3)=[O:15])[C@H:11]([C:27](O)=[O:28])[CH2:10]2)=[CH:5][CH:4]=1.C(Cl)(=O)C(C)(C)C.FC(F)(F)C(O)=O.[N:46]1([C@H:51]2[CH2:55][CH2:54][NH:53][CH2:52]2)[CH:50]=[N:49][CH:48]=[N:47]1>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][S:8][C@@H:9]2[CH2:13][N:12]([C:14]([O:16][CH2:17][C:18]3[CH:19]=[CH:20][C:21]([N+:24]([O-:26])=[O:25])=[CH:22][CH:23]=3)=[O:15])[C@H:11]([C:27]([N:53]3[CH2:54][CH2:55][C@H:51]([N:46]4[CH:50]=[N:49][CH:48]=[N:47]4)[CH2:52]3)=[O:28])[CH2:10]2)=[CH:30][CH:31]=1

Participants

4

Reactant 3

HCID 62493Pivaloyl chlorideHCID 15297071(2S,4S)-4-(4-methoxybenzyl)thio-1-(4-nitrobenzyloxycarbonyl)-L-prolineHCID 22881680HCID 22881680, compound

Product 1

HCID 67585187HCID 67585187, compoundYield 150.2%

Procedure

Following a procedure similar to that described in Preparation 18(a), but using 768 mg of (2S,4S)-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)-2-pyrrolidinecarboxylic acid, 218 mg of pivaloyl chloride and 238 mg of (3S)-3-(1,2,4-triazol-1-yl)pyrrolidine trifluoroacetate, 803 mg of the title compound were obtained as a powder.

Sources & evidence

ORD record
ord-ace86e9a2ce445a49f0ee05cfdf8b651
Source dataset
uspto-grants-1998_01
Patent number
US05712267

Reaction notes

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