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

HRID 396893Notes

Reaction equation

HRID 396893 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@H:12]([C:35]([OH:37])=[O:36])[CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]([O:20]CC2C3C=CC=CC=3C3C2=CC=CC=3)=O)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:38]([NH:46][C@H:47](C(O)=O)[CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)(=[O:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]([C@H:12]([C:35]([OH:37])=[O:36])[CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]([C@@H:47]([NH:46][C:38]([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)=[O:45])[CH2:48][C:49]2[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=2)=[O:20])[CH2:1][CH:2]([CH3:7])[CH3:3])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 97370Benzoyl-L-phenylalanineHCID 3013740(2S)-6-(9H-fluoren-9-ylmethoxycarbonylamino)-2-(p-tolylsulfonylamino)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-N(-(4-methylbenzenesulfonyl)-Nε-(9-fluorenylmethoxycarbonyl)-L-lysine as described in general procedure Bb using Nα-benzoyl-L-phenylalanine (321 mg, 1.2 mmol). 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-aead5722998e416893f2ea4bbf3ccbd1
Source dataset
uspto-grants-2003_08
Patent number
US06608100B1

Reaction notes

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