Pivaloyl chloride → HCID 10951955, compound

HRID 727654Notes

Reaction equation

COC1C=CC(C[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]([OH:29])=O)[CH2:10]2)=CC=1.C(Cl)(=O)C(C)(C)C.FC(F)(F)C(O)=O.[N+:46]([C:49]1[CH:64]=[CH:63][C:52]([CH2:53][O:54][C:55]([NH:57][C@@H:58]2[CH2:62][CH2:61][NH:60][CH2:59]2)=[O:56])=[CH:51][CH:50]=1)([O-:48])=[O:47]>>[SH:8][C@@H:9]1[CH2:13][N:12]([C:14]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][C:21]([N+:24]([O-:26])=[O:25])=[CH:22][CH:23]=2)=[O:15])[C@H:11]([C:27]([N:60]2[CH2:61][CH2:62][C@@H:58]([NH:57][C:55]([O:54][CH2:53][C:52]3[CH:63]=[CH:64][C:49]([N+:46]([O-:48])=[O:47])=[CH:50][CH:51]=3)=[O:56])[CH2:59]2)=[O:29])[CH2:10]1

Participants

Reactant 3

HCID 62493Pivaloyl chloride

HCID 15297071(2S,4S)-4-(4-methoxybenzyl)thio-1-(4-nitrobenzyloxycarbonyl)-L-proline

HCID 67586387HCID 67586387, compound

Product 1

HCID 10951955HCID 10951955, compoundYield 65.8%

Procedure

Following a procedure similar to that described in Preparation 18, but using 1.29 g of (2S,4S)-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)-2-pyrrolidinecarboxylic acid, 365 mg of pivaloyl chloride and 1.14 g of (3R)-3-(4-nitrobenzyloxycarbonyl)aminopyrrolidine trifluoroacetate, 1.09 g of the title compound were obtained as a powder.

Workup

customthat described in Preparation 18

Sources & evidence

ORD record: ord-d2f835f5eaf84ef1a4382d923d62a93f
Source dataset: uspto-grants-1998_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05712267

Reaction notes

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