(S)-2-(4-acetamidophenylsulfonamido)-3-phenylpropanoic acid → (2S)-6-[[(2S)-2-[(4-acetamidophenyl)sulfonylamino]-3-phenyl-propanoyl]amino]-2-[isobutyl-(4-nitrophenyl)sulfonyl-amino]hexanoic acid

HRID 396879Notes

Reaction equation

HRID 396879 reaction equation
[CH2:1]([N:5]([S:32]([C:35]1[CH:40]=[CH:39][C:38]([N+:41]([O-:43])=[O:42])=[CH:37][CH:36]=1)(=[O:34])=[O:33])[C@H:6]([C:29]([OH:31])=[O:30])[CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12](OCC1C2C=CC=CC=2C2C1=CC=CC=2)=[O:13])[CH:2]([CH3:4])[CH3:3].[C:44]([NH:47][C:48]1[CH:53]=[CH:52][C:51]([S:54]([NH:57][C@H:58](C(O)=O)[CH2:59][C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)(=[O:56])=[O:55])=[CH:50][CH:49]=1)(=[O:46])[CH3:45]>>[CH3:3][CH:2]([CH2:1][N:5]([S:32]([C:35]1[CH:36]=[CH:37][C:38]([N+:41]([O-:43])=[O:42])=[CH:39][CH:40]=1)(=[O:33])=[O:34])[C@H:6]([C:29]([OH:31])=[O:30])[CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12]([C@@H:58]([NH:57][S:54]([C:51]1[CH:50]=[CH:49][C:48]([NH:47][C:44]([CH3:45])=[O:46])=[CH:53][CH:52]=1)(=[O:56])=[O:55])[CH2:59][C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1)=[O:13])[CH3:4]

Participants

3

Reactant 2

HCID 983566(S)-2-(4-acetamidophenylsulfonamido)-3-phenylpropanoic acidHCID 3013754(2S)-6-(9H-fluoren-9-ylmethoxycarbonylamino)-2-[isobutyl-(4-nitrophenyl)sulfonyl-amino]hexanoic acid

Product 1

HCID 508551(2S)-6-[[(2S)-2-[(4-acetamidophenyl)sulfonylamino]-3-phenyl-propanoyl]amino]-2-[isobutyl-(4-nitrophenyl)sulfonyl-amino]hexanoic acid

Procedure

The title compound was prepared from solid phase bound Nα-isobutyl-Nα-(4-nitrobenzenesulfonyl)-Nε-(9-fluorenylmethoxycarbonyl)-L-lysine (step A) as described in general procedure Bb using Nα-(4-acetamidobenzenesulfonyl)-L-phenylalanine (400 mg, 1.2 mmol) which was prepared in step A of example 3. The final product was purified by preparative HPLC to yield 55 mg (60%) of the desired material.

Workup

  1. customwas prepared in step A of example 3
  2. customThe final product was purified by preparative HPLC

Sources & evidence

ORD record
ord-2b2270c96c614a34a531edea8b1302df
Source dataset
uspto-grants-2003_08
Patent number
US06608100B1

Reaction notes

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