N-[(4-Methylphenyl)sulfonyl]-L-glutamic acid → (2S)-6-[[(2S)-5-hydroxy-5-oxo-2-(p-tolylsulfonylamino)pentanoyl]amino]-2-[isobutyl(p-tolylsulfonyl)amino]hexanoic acid

HRID 396882Notes

Reaction equation

HRID 396882 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(OCC1C2C=CC=CC=2C2C1=CC=CC=2)=O)[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:59]([OH:61])=O)[CH2:54][CH2:55][C:56]([OH:58])=[O:57])(=[O:51])=[O:50])=[CH:45][CH:44]=1>>[CH3:42][C:43]1[CH:44]=[CH:45][C:46]([S:49]([NH:52][C@H:53]([C:59]([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:61])[CH2:54][CH2:55][C:56]([OH:58])=[O:57])(=[O:50])=[O:51])=[CH:47][CH:48]=1

Participants

3

Reactant 2

HCID 2063452N-[(4-Methylphenyl)sulfonyl]-L-glutamic acidHCID 3013742(2S)-6-(9H-fluoren-9-ylmethoxycarbonylamino)-2-[isobutyl(p-tolylsulfonyl)amino]hexanoic acid

Product 1

HCID 508561(2S)-6-[[(2S)-5-hydroxy-5-oxo-2-(p-tolylsulfonylamino)pentanoyl]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-glutamic acid (360 mg, 1.2 mmol) prepared in step A of this example. The final product was purified by preparative HPLC to yield 20 mg (25%) of the desired material.

Workup

  1. customThe final product was purified by preparative HPLC

Sources & evidence

ORD record
ord-24af986e38214a32b2525a1fe783b1b0
Source dataset
uspto-grants-2003_08
Patent number
US06608100B1

Reaction notes

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