L-Threonine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)- → (2S)-6-[[(2S,3R)-3-benzyloxy-2-(tert-butoxycarbonylamino)butanoyl]amino]-2-[isobutyl(p-tolylsulfonyl)amino]hexanoic acid

HRID 1839510Notes

Reaction equation

HRID 1839510 reaction equation
C([NH:5][CH2:6][CH2:7][CH2:8][CH2:9][C@@H:10]([C:22]([OH:24])=[O:23])[NH:11][S:12]([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)(=[O:14])=[O:13])C(C)C.[C:25]([O:29][C:30]([NH:32][C@H:33]([C:44]([OH:46])=O)[C@@H:34]([CH3:43])[O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:31])([CH3:28])([CH3:27])[CH3:26]>>[CH3:21][C:18]1[CH:17]=[CH:16][C:15]([S:12]([N:11]([C@H:10]([C:22]([OH:24])=[O:23])[CH2:9][CH2:8][CH2:7][CH2:6][NH:5][C:44]([C@@H:33]([NH:32][C:30]([O:29][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:31])[C@H:34]([O:35][CH2:36][C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH3:43])=[O:46])[CH2:17][CH:18]([CH3:21])[CH3:19])(=[O:13])=[O:14])=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 1549483L-Threonine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-HCID 131724231Nepsilon-isobutyl-Nalpha-(4-methylbenzenesulfonyl)-L-lysine

Product 1

HCID 5495869(2S)-6-[[(2S,3R)-3-benzyloxy-2-(tert-butoxycarbonylamino)butanoyl]amino]-2-[isobutyl(p-tolylsulfonyl)amino]hexanoic acid

Procedure

The title compound was prepared from Nε-isobutyl-Nα-(4-methylbenzenesulfonyl)-L-lysine (100 mg, 0.29 mmol, example 1, step E) as described in general procedure Bc using commercially available Nα-tert-butoxycarbonyl-O-benzyl-L-threonine (93 mg, 0.3 mmol). The final product was triturated with ether to yield 195 mg (98%) of the desired material.

Workup

  1. customThe final product was triturated with ether

Sources & evidence

ORD record
ord-1a095b3fc86f4106a6da05a445df4aaf
Source dataset
uspto-grants-2004_01
Patent number
US06677367B2

Reaction notes

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