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

HRID 1839503Notes

Reaction equation

HRID 1839503 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]([NH:33][C@H:34]([C:39](O)=[O:40])[CH2:35][C:36](=[O:38])[NH2:37])(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[CH3:24][C:21]1[CH:22]=[CH:23][C:18]([S:15]([N:5]([C@H:6]([C:12]([OH:14])=[O:13])[CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:39]([C@@H:34]([NH:33][C:25]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:32])[CH2:35][C:36]([NH2:37])=[O:38])=[O:40])[CH2:1][CH:2]([CH3:3])[CH3:4])(=[O:17])=[O:16])=[CH:19][CH:20]=1

Participants

3

Reactant 2

HCID 7062826N-Benzoyl-L-asparagineHCID 23552860Nalpha-isobutyl-Nalpha-(4-methylbenzenesulfonyl)-L-lysine

Product 1

HCID 508586(2S)-6-[[(2S)-4-amino-2-benzamido-4-oxo-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-benzoyl-L-asparagine (70 mg, 0.3 mmol) which was prepared in step A this example. The final product was purified by preparative HPLC to yield 14 mg (9%) of the desired material.

Workup

  1. customwas prepared in step A this example
  2. customThe final product was purified by preparative HPLC

Sources & evidence

ORD record
ord-27b2713f5d0e4174a029e03ffef3ab72
Source dataset
uspto-grants-2004_01
Patent number
US06677367B2

Reaction notes

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