Pivaloyl chloride → HCID 11146331, compound

HRID 362036Notes

Reaction equation

HRID 362036 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.[CH3:46][N:47]([C@H:61]1[CH2:65][CH2:64][NH:63][CH2:62]1)[C:48]([O:50][CH2:51][C:52]1[CH:57]=[CH:56][C:55]([N+:58]([O-:60])=[O:59])=[CH:54][CH:53]=1)=[O:49]>>[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:63]2[CH2:64][CH2:65][C@H:61]([N:47]([CH3:46])[C:48]([O:50][CH2:51][C:52]3[CH:57]=[CH:56][C:55]([N+:58]([O-:60])=[O:59])=[CH:54][CH:53]=3)=[O:49])[CH2:62]2)=[O:29])[CH2:10]1

Participants

4

Reactant 3

HCID 62493Pivaloyl chlorideHCID 15297071(2S,4S)-4-(4-methoxybenzyl)thio-1-(4-nitrobenzyloxycarbonyl)-L-prolineHCID 70273891HCID 70273891, compound

Product 1

HCID 11146331HCID 11146331, compoundYield 76%

Procedure

Following a procedure similar to that described in Preparation 18, but using 1.21 g of (2S,4S)-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)-2-pyrrolidinecarboxylic acid, 343 mg of pivaloyl chloride and 1.27 g of (3S)-3-[N-methyl-N-(4-nitrobenzyloxycarbonyl)amino]pyrrolidine trifluoroacetate, 1.21 g of the title compound were obtained as a powder.

Workup

  1. customthat described in Preparation 18

Sources & evidence

ORD record
ord-d2090dc43e954a5ab7a12fb8cd3d74a8
Source dataset
uspto-grants-1999_02
Patent number
US05866564

Reaction notes

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