HCID 744894, compound → L-Lysine

HRID 1634653Notes

Reaction equation

HRID 1634653 reaction equation
[CH2:1]([N:5]([S:15]([C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][CH:19]=1)(=[O:17])=[O:16])[C@H:6]([C:12]([OH:14])=[O:13])[CH2:7][CH2:8][CH2:9][CH2:10][NH2:11])[CH:2]([CH3:4])[CH3:3].[C:27]1([S:33]([NH:36][C@H:37]([C:45](O)=[O:46])[CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)(=[O:35])=[O:34])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>>[NH2:24][C:21]1[CH:22]=[CH:23][C:18]([S:15]([N:5]([CH2:1][CH:2]([CH3:4])[CH3:3])[C@H:6]([C:12]([OH:14])=[O:13])[CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:45](=[O:46])[C@H:37]([CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[NH:36][S:33]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)(=[O:35])=[O:34])(=[O:17])=[O:16])=[CH:19][CH:20]=1.[NH2:5][C@H:6]([C:12]([OH:14])=[O:13])[CH2:7][CH2:8][CH2:9][CH2:10][NH2:11]

Participants

4

Reactant 2

HCID 744894HCID 744894, compoundHCID 69107391HCID 69107391, compound

Product 2

HCID 5962L-LysineHCID 508567HCID 508567, compound

Procedure

The title compound was prepared from Nα-isobutyl-Nα-(4-nitrobenzenesulfonyl)-L-lysine (385 mg, 1.0 mmol, example 5, step C) as described in general procedure Bc using Nα-benzenesulfonyl-L-phenylalanine (335 mg, 1.1 mmol) which was prepared in step A of example 8. The final product was purified by preparative HPLC to yield 550 mg (85%) of Nα-(4-nitrobenzenesulfonyl)-Nα-isobutyl-Nε-(Nα-benzenesulfonyl)-L-phenylalanyl)-L-lysine. The latter derivative (200 mg) was hydrogenolysed following the indications of general procedure E. Purification by HPLC gave the desired material (129 mg, 65%).

Workup

  1. customwas prepared in step A of example 8
  2. customThe final product was purified by preparative HPLC

Sources & evidence

ORD record
ord-a3db85c950504b2daaf80b51a2bd10bb
Source dataset
uspto-grants-2003_01
Patent number
US06506786B2

Reaction notes

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