4-(N-Boc-amino)piperidine → (2S,4S)-4-Mercapto-2-[4-(N-4-nitrobenzyloxycarbonylacetimidoyl)aminopiperidin-1-ylcarbonyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

HRID 362050Notes

Reaction equation

HRID 362050 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(OC(N[CH:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1)=O)(C)(C)C.[N+:46]([C:49]1[CH:62]=[CH:61][C:52]([CH2:53][O:54][C:55]([NH:57][C:58](=[NH:60])[CH3:59])=[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:43]2[CH2:44][CH2:45][CH:40]([NH:60][C:58](=[N:57][C:55]([O:54][CH2:53][C:52]3[CH:51]=[CH:50][C:49]([N+:46]([O-:48])=[O:47])=[CH:62][CH:61]=3)=[O:56])[CH3:59])[CH2:41][CH2:42]2)=[O:29])[CH2:10]1

Participants

4

Reactant 3

HCID 7238334-(N-Boc-amino)piperidineHCID 15297071(2S,4S)-4-(4-methoxybenzyl)thio-1-(4-nitrobenzyloxycarbonyl)-L-prolineHCID 140352007HCID 140352007, compound

Product 1

HCID 178465420(2S,4S)-4-Mercapto-2-[4-(N-4-nitrobenzyloxycarbonylacetimidoyl)aminopiperidin-1-ylcarbonyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidineYield 97.3%

Procedure

Following a procedure similar to that described in Preparation 1, but using 446 mg of (2S,4S)-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)-2-pyrrolidinecarboxylic acid, 220 mg of 4-t-butoxycarbonylaminopiperidine and 119 mg of N-(4-nitrobenzyloxycarbonyl)acetamidine, 307 mg of the title compound were obtained as a powder.

Workup

  1. customthat described in Preparation 1

Sources & evidence

ORD record
ord-6b1190d03cfc4a028d2a39f76e5e8279
Source dataset
uspto-grants-1999_02
Patent number
US05866564

Reaction notes

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