Benzoyl-L-phenylalanine → (2S)-6-[[(2S)-2-benzamido-3-phenyl-propanoyl]amino]-2-[isobutyl(p-tolylsulfonyl)amino]hexanoic acid

HRID 431324Notes

Reaction equation

HRID 431324 reaction equation
[CH2:1]([N:5]([S:32]([C:35]1[CH:40]=[CH:39][C:38]([CH3:41])=[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:42]([NH:50][C@H:51](C(O)=O)[CH2:52][C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)(=[O:49])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>>[CH3:41][C:38]1[CH:39]=[CH:40][C:35]([S:32]([N:5]([C@H:6]([C:29]([OH:31])=[O:30])[CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12]([C@@H:51]([NH:50][C:42]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[O:49])[CH2:52][C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)=[O:13])[CH2:1][CH:2]([CH3:4])[CH3:3])(=[O:33])=[O:34])=[CH:36][CH:37]=1

Participants

3

Reactant 2

HCID 97370Benzoyl-L-phenylalanineHCID 3013742(2S)-6-(9H-fluoren-9-ylmethoxycarbonylamino)-2-[isobutyl(p-tolylsulfonyl)amino]hexanoic acid

Product 1

HCID 508573(2S)-6-[[(2S)-2-benzamido-3-phenyl-propanoyl]amino]-2-[isobutyl(p-tolylsulfonyl)amino]hexanoic acid

Procedure

The title compound was prepared from solid phase bound Nα-isobutyl-Nα-(4-methylbenzenesulfonyl)-Nε-(9-fluorenylmethoxycarbonyl)-L-lysine as described in general procedure Bb using Nα-benzoyl-L-phenylalanine (321 mg, 1.2 1mmol). The final product was purified by preparative HPLC to yield 44 mg (58%) of the desired material.

Workup

  1. customThe final product was purified by preparative HPLC

Sources & evidence

ORD record
ord-47149169eff14a44aa31209d3d0b35da
Source dataset
uspto-grants-2003_12
Patent number
US06656965B2

Reaction notes

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