N-(2-Thienylsulfonyl)-L-phenylalanine → (2S)-2-[isobutyl-(4-nitrophenyl)sulfonyl-amino]-6-[[(2S)-3-phenyl-2-(2-thienylsulfonylamino)propanoyl]amino]hexanoic acid

HRID 1634645Notes

Reaction equation

HRID 1634645 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].[S:44]1[CH:48]=[CH:47][CH:46]=[C:45]1[S:49]([NH:52][C@H:53](C(O)=O)[CH2:54][C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)(=[O:51])=[O:50]>>[CH3:4][CH:2]([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: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:53]([NH:52][S:49]([C:45]1[S:44][CH:48]=[CH:47][CH:46]=1)(=[O:51])=[O:50])[CH2:54][C:55]1[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=1)=[O:13])[CH3:3]

Participants

3

Reactant 2

HCID 704092N-(2-Thienylsulfonyl)-L-phenylalanineHCID 3013754(2S)-6-(9H-fluoren-9-ylmethoxycarbonylamino)-2-[isobutyl-(4-nitrophenyl)sulfonyl-amino]hexanoic acid

Product 1

HCID 508552(2S)-2-[isobutyl-(4-nitrophenyl)sulfonyl-amino]-6-[[(2S)-3-phenyl-2-(2-thienylsulfonylamino)propanoyl]amino]hexanoic acid

Procedure

The title compound was prepared from solid phase bound Nα-isobutyl-Nα-(4-nitrobenzenesulfonyl)-Nε-(9-fluorenylmethoxycarbonyl)-L-lysine as described in general procedure Bb using Nα-(2-thiophenesulfonyl)-L-phenylalanine (300 mg, 1.2 mmol) which was prepared in step A of example 24. The final product was purified by preparative HPLC to yield 46 mg (54%) of the desired material.

Workup

  1. customwas prepared in step A of example 24
  2. customThe final product was purified by preparative HPLC

Sources & evidence

ORD record
ord-a0ba05ad15474a48aa58dfc8923f0d54
Source dataset
uspto-grants-2003_01
Patent number
US06506786B2

Reaction notes

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