(2S)-3-Hydroxy-2-(4-methylbenzenesulfonamido)propanoic acid → (2S)-6-[[(2S)-3-hydroxy-2-(p-tolylsulfonylamino)propanoyl]amino]-2-[isobutyl(p-tolylsulfonyl)amino]hexanoic acid

HRID 431314Notes

Reaction equation

HRID 431314 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].[CH3:42][C:43]1[CH:48]=[CH:47][C:46]([S:49]([NH:52][C@H:53](C(O)=O)[CH2:54][OH:55])(=[O:51])=[O:50])=[CH:45][CH:44]=1>>[CH3:42][C:43]1[CH:48]=[CH:47][C:46]([S:49]([NH:52][C@H:53]([C:12]([NH:11][CH2:10][CH2:9][CH2:8][CH2:7][C@H:6]([N:5]([S:32]([C:35]2[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][CH:36]=2)(=[O:34])=[O:33])[CH2:1][CH:2]([CH3:4])[CH3:3])[C:29]([OH:31])=[O:30])=[O:13])[CH2:54][OH:55])(=[O:51])=[O:50])=[CH:45][CH:44]=1

Participants

3

Reactant 2

HCID 774825(2S)-3-Hydroxy-2-(4-methylbenzenesulfonamido)propanoic acidHCID 3013742(2S)-6-(9H-fluoren-9-ylmethoxycarbonylamino)-2-[isobutyl(p-tolylsulfonyl)amino]hexanoic acid

Product 1

HCID 508555(2S)-6-[[(2S)-3-hydroxy-2-(p-tolylsulfonylamino)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-(4-methylbenzenesulfonyl)-L-serine (150 mg, 1.2 mmol) prepared in step A of this example. The final product was purified by preparative HPLC to yield 35 mg (46%) of the desired material.

Workup

  1. customThe final product was purified by preparative HPLC

Sources & evidence

ORD record
ord-9aeb14f72c444c2b979ac3ed04a188b6
Source dataset
uspto-grants-2003_12
Patent number
US06656965B2

Reaction notes

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