(S)-2-methoxycarbonylamino-3,3-diphenyl-propionic acid → methyl N-[(1S)-1-[[(4S)-4-[(4-aminophenyl)sulfonyl-isobutyl-amino]-5-hydroxy-pentyl]carbamoyl]-2,2-diphenyl-ethyl]carbamate

HRID 987946Notes

Reaction equation

HRID 987946 reaction equation
[CH3:1][O:2][C:3]([NH:5][C@@H:6]([CH:10]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:7]([OH:9])=O)=[O:4].[NH2:23][C:24]1[CH:29]=[CH:28][C:27]([S:30]([N:33]([C@H:38]([CH2:43][OH:44])[CH2:39][CH2:40][CH2:41][NH2:42])[CH2:34][CH:35]([CH3:37])[CH3:36])(=[O:32])=[O:31])=[CH:26][CH:25]=1>>[CH3:1][O:2][C:3](=[O:4])[NH:5][C@H:6]([C:7](=[O:9])[NH:42][CH2:41][CH2:40][CH2:39][C@H:38]([N:33]([S:30]([C:27]1[CH:26]=[CH:25][C:24]([NH2:23])=[CH:29][CH:28]=1)(=[O:32])=[O:31])[CH2:34][CH:35]([CH3:36])[CH3:37])[CH2:43][OH:44])[CH:10]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

3

Reactant 2

HCID 10017620(S)-2-methoxycarbonylamino-3,3-diphenyl-propionic acidHCID 12986160(1S)-4-Amino-N-(4-amino-1-hydroxymethyl-butyl)-N-isobutyl-benzenesulfonamide

Product 1

HCID 513932methyl N-[(1S)-1-[[(4S)-4-[(4-aminophenyl)sulfonyl-isobutyl-amino]-5-hydroxy-pentyl]carbamoyl]-2,2-diphenyl-ethyl]carbamate

Procedure

The title compound was prepared from general procedure A using (2S)-2-methoxycarbonylamino-3,3-diphenyl-propionic acid (see example 34, step A) and amine intermediate VII. The final product was obtained in 74% yield. Rf=0.57 EtOAc 100%.

Sources & evidence

ORD record
ord-b3caa8a532fc4e15b0654d7ab53ba982
Source dataset
uspto-grants-2003_10
Patent number
US06632816B1

Reaction notes

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