Tosyl-L-asparagine → (2S)-6-[[(2S)-4-amino-4-oxo-2-(p-tolylsulfonylamino)butanoyl]amino]-2-[isobutyl(p-tolylsulfonyl)amino]hexanoic acid

HRID 396899Notes

Reaction equation

HRID 396899 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].[CH3:25][C:26]1[CH:31]=[CH:30][C:29]([S:32]([NH:35][C@H:36]([C:41](O)=[O:42])[CH2:37][C:38](=[O:40])[NH2:39])(=[O:34])=[O:33])=[CH:28][CH:27]=1>>[CH3:25][C:26]1[CH:31]=[CH:30][C:29]([S:32]([NH:35][C@H:36]([C:41]([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:42])[CH2:37][C:38]([NH2:39])=[O:40])(=[O:33])=[O:34])=[CH:28][CH:27]=1

Participants

3

Reactant 2

HCID 6995570Tosyl-L-asparagineHCID 23552860Nalpha-isobutyl-Nalpha-(4-methylbenzenesulfonyl)-L-lysine

Product 1

HCID 508584(2S)-6-[[(2S)-4-amino-4-oxo-2-(p-tolylsulfonylamino)butanoyl]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 Nα-(4-methylbenzenesulfonyl)-L-asparagine (90 mg, 0.3 mmol) which was prepared in step A of example 47. The final product was triturated with ether to yield 95 mg (15%) of the desired material.

Workup

  1. customwas prepared in step A of example 47
  2. customThe final product was triturated with ether

Sources & evidence

ORD record
ord-7b746c76e9954b4eba32adb59001a1d1
Source dataset
uspto-grants-2003_08
Patent number
US06608100B1

Reaction notes

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