Nalpha-isobutyl-Nalpha-(4-methylbenzenesulfonyl)-L-lysine → (2S)-6-[[(2S)-4-amino-2-(2,2-dimethylpropanoylamino)-4-oxo-butanoyl]amino]-2-[isobutyl(p-tolylsulfonyl)amino]hexanoic acid

HRID 431329Notes

Reaction equation

HRID 431329 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:31][C@H:32]([C:37](O)=[O:38])[CH2:33][C:34](=[O:36])[NH2:35])(=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27]>>[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:37]([C@@H:32]([NH:31][C:25]([C:26]([CH3:29])([CH3:28])[CH3:27])=[O:30])[CH2:33][C:34]([NH2:35])=[O:36])=[O:38])[CH2:1][CH:2]([CH3:3])[CH3:4])(=[O:17])=[O:16])=[CH:19][CH:20]=1

Participants

3

Reactant 2

HCID 23552860Nalpha-isobutyl-Nalpha-(4-methylbenzenesulfonyl)-L-lysineHCID 30053119Nalpha-pivaloyl-l-asparagine

Product 1

HCID 508585(2S)-6-[[(2S)-4-amino-2-(2,2-dimethylpropanoylamino)-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-pivaloyl-L-asparagine (65 mg, 0.3 mmol) which was prepared in step A this example. The final product was purified by preparative HPLC to yield 21 mg (12%) 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-1b000c4866444b9bb0b6c994bfc8fda4
Source dataset
uspto-grants-2003_12
Patent number
US06656965B2

Reaction notes

Loading…