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 431336Notes

Reaction equation

HRID 431336 reaction equation
[CH2:1]([N:5]([S:15]([C:18]1[CH:23]=[CH:22][C:21]([CH2:24]C)=[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:26]([O:30][C:31]([NH:33][C@H:34]([C:45]([OH:47])=O)[CH2:35][S:36][CH2:37][C:38]1[CH:43]=[CH:42][C:41]([CH3:44])=[CH:40][CH:39]=1)=[O:32])([CH3:29])([CH3:28])[CH3:27]>>[CH3:44][C:41]1[CH:40]=[CH:39][C:38]([CH2:37][S:36][CH2:35][C@H:34]([NH:33][C:31]([O:30][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:32])[C:45]([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]([CH3:4])[CH3:3])[C:12]([OH:14])=[O:13])=[O:47])=[CH:43][CH:42]=1

Participants

3

Reactant 2

HCID 7010551N-alpha-t-Butyloxycarbonyl-S-(4-methyl-benzyl)-L-cysteineHCID 69929831Nalpha-isobutyl-Nalpha-(4-ethylbenzenesulfonyl)-L-ysine

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-ethylbenzenesulfonyl)-L-ysine (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-3c5995ee499746b8bb319452d26904ee
Source dataset
uspto-grants-2003_12
Patent number
US06656965B2

Reaction notes

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