N-alpha-t-Butyloxycarbonyl-S-(4-methyl-benzyl)-L-cysteine → (2S)-6-[[(2R)-2-(tert-butoxycarbonylamino)-3-(p-tolylmethylsulfanyl)propanoyl]amino]-2-[isobutyl(p-tolylsulfonyl)amino]hexanoic acid

HRID 1634672Notes

Reaction equation

HRID 1634672 reaction equation
[CH2:1]([N:5]([S:15]([C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=1)(=[O:17])=[O:16])[C@H:6]([C:12]([OH:14])=[O:13])[CH2:7][CH2:8][CH2:9][CH2:10][NH2:11])[CH:2]([CH3:4])[CH3:3].[C:25]([O:29][C:30]([NH:32][C@H:33]([C:44](O)=[O:45])[CH2:34][S:35][CH2:36][C:37]1[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][CH:38]=1)=[O:31])([CH3:28])([CH3:27])[CH3:26]>>[CH3:43][C:40]1[CH:39]=[CH:38][C:37]([CH2:36][S:35][CH2:34][C@H:33]([NH:32][C:30]([O:29][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:31])[C:44]([NH:11][CH2:10][CH2:9][CH2:8][CH2:7][C@H:6]([N:5]([S:15]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[CH2:1][CH:2]([CH3:3])[CH3:4])[C:12]([OH:14])=[O:13])=[O:45])=[CH:42][CH:41]=1

Participants

3

Reactant 2

HCID 7010551N-alpha-t-Butyloxycarbonyl-S-(4-methyl-benzyl)-L-cysteineHCID 23552860Nalpha-isobutyl-Nalpha-(4-methylbenzenesulfonyl)-L-lysine

Product 1

HCID 508604(2S)-6-[[(2R)-2-(tert-butoxycarbonylamino)-3-(p-tolylmethylsulfanyl)propanoyl]amino]-2-[isobutyl(p-tolylsulfonyl)amino]hexanoic acid

Procedure

The title compound was prepared from Nα-isobutyl-Nα-(4-methylbenzenesulfonyl)-L-lysine (100 mg, 0.29 mmol, example 1, step E) as described in general procedure Bc using commercially available Nα-tert-butoxycarbonyl-S-(4-methylbenzyl)-L-cysteine (67 mg, 0.3 mmol). The final product was triturated with ether to yield 130 mg (65%) of the desired material.

Workup

  1. customThe final product was triturated with ether

Sources & evidence

ORD record
ord-16e2a0b64de949378ca1dae57f87c1c1
Source dataset
uspto-grants-2003_01
Patent number
US06506786B2

Reaction notes

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