2,2-Dimethylpiperazine → (2S,4S)-2-[3,3-Dimethyl-4-(4-nitrobenzyloxycarbonyl)-1-piperazinylcarbonyl]-4-mercapto-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

HRID 362055Notes

Reaction equation

HRID 362055 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.[CH3:32][C:33]1([CH3:39])[CH2:38][NH:37][CH2:36][CH2:35][NH:34]1>>[CH3:32][C:33]1([CH3:39])[N:34]([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])[CH2:35][CH2:36][N:37]([C:27]([C@@H:11]2[CH2:10][C@H:9]([SH:8])[CH2:13][N:12]2[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])=[O:29])[CH2:38]1

Participants

3

Reactant 2

HCID 146641862,2-DimethylpiperazineHCID 15297071(2S,4S)-4-(4-methoxybenzyl)thio-1-(4-nitrobenzyloxycarbonyl)-L-proline

Product 1

HCID 88319373(2S,4S)-2-[3,3-Dimethyl-4-(4-nitrobenzyloxycarbonyl)-1-piperazinylcarbonyl]-4-mercapto-1-(4-nitrobenzyloxycarbonyl)pyrrolidineYield 106%

Procedure

Following a procedure similar to that described in Preparation 38, but using 0.35 g of (2S,4S)-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)-2-pyrrolidinecarboxylic acid, 0.15 g of N,N'-carbonyldiimidazole and 0.13 g of 2,2-dimethylpiperazine, 250 mg of the title compound were obtained as an amorphous solid.

Workup

  1. customthat described in Preparation 38

Sources & evidence

ORD record
ord-4c708044b26c4799bd842852fec35648
Source dataset
uspto-grants-1999_02
Patent number
US05866564

Reaction notes

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