Pivaloyl chloride → HCID 11143993, compound

HRID 362052Notes

Reaction equation

COC1C=CC(C[S:8][C@@H:9]2[CH2:13][N:12]([CH3:14])[C@H:11]([C:15]([OH:17])=O)[CH2:10]2)=CC=1.C(Cl)(=O)C(C)(C)C.FC(F)(F)C(O)=O.[N+:34]([C:37]1[CH:52]=[CH:51][C:40]([CH2:41][O:42][C:43]([NH:45][C@H:46]2[CH2:50][CH2:49][NH:48][CH2:47]2)=[O:44])=[CH:39][CH:38]=1)([O-:36])=[O:35]>>[SH:8][C@@H:9]1[CH2:13][N:12]([CH3:14])[C@H:11]([C:15]([N:48]2[CH2:49][CH2:50][C@H:46]([NH:45][C:43]([O:42][CH2:41][C:40]3[CH:51]=[CH:52][C:37]([N+:34]([O-:36])=[O:35])=[CH:38][CH:39]=3)=[O:44])[CH2:47]2)=[O:17])[CH2:10]1

Participants

Reactant 3

HCID 62493Pivaloyl chloride

HCID 15297072HCID 15297072, compound

HCID 67586712HCID 67586712, compound

Product 1

HCID 11143993HCID 11143993, compoundYield 71.6%

Procedure

Following a procedure similar to that described in Preparation 18, but using 1.03 g of (2S,4S)-4-(4-methoxybenzylthio)-1-methyl-2-pyrrolidinecarboxylic acid, 463 mg of pivaloyl chloride and 1.45 g of (3S)-3-(4-nitrobenzyloxycarbonyl)aminopyrrolidine trifluoroacetate, 1.07 g of the title compound were obtained as a powder.

Workup

customthat described in Preparation 18

Sources & evidence

ORD record: ord-124d1006aa94472386b7e5e7683f6003
Source dataset: uspto-grants-1999_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05866564

Reaction notes

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