Pivaloyl chloride → HCID 86751994, compound

HRID 362028Notes

Reaction equation

HRID 362028 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.[CH3:39][C@H:40]1[CH2:45][NH:44][C@H:43]([CH3:46])[CH2:42][N:41]1[C:47]([O:49][CH2:50][C:51]1[CH:56]=[CH:55][C:54]([N+:57]([O-:59])=[O:58])=[CH:53][CH:52]=1)=[O:48]>C(N(CC)CC)C>[CH3:46][C@H:43]1[CH2:42][N:41]([C:47]([O:49][CH2:50][C:51]2[CH:56]=[CH:55][C:54]([N+:57]([O-:59])=[O:58])=[CH:53][CH:52]=2)=[O:48])[C@H:40]([CH3:39])[CH2:45][N:44]1[C:27]([C@@H:11]1[CH2:10][C@H:9]([SH:8])[CH2:13][N:12]1[C:14]([O:16][CH2:17][C:18]1[CH:19]=[CH:20][C:21]([N+:24]([O-:26])=[O:25])=[CH:22][CH:23]=1)=[O:15])=[O:29]

Participants

5

Reactant 3

HCID 62493Pivaloyl chlorideHCID 15297071(2S,4S)-4-(4-methoxybenzyl)thio-1-(4-nitrobenzyloxycarbonyl)-L-prolineHCID 67586047HCID 67586047, compound

Product 1

HCID 86751994HCID 86751994, compoundYield 23.9%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Following a procedure similar to that described in Preparation 8, but using 1.79 g of (2S,4S)-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)-2-pyrrolidinecarboxylic acid, 0.54 ml of pivaloyl chloride, 0.61 ml of triethylamine and 1.29 g of trans-2,5-dimethyl-1-(4-nitrobenzyloxycarbonyl)piperazine, 577 mg of the title compound were obtained as an amorphous solid.

Workup

  1. customthat described in Preparation 8

Sources & evidence

ORD record
ord-e1ecb8764e9348d29b94c61f0e9743c3
Source dataset
uspto-grants-1999_02
Patent number
US05866564

Reaction notes

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