(1S)-4-Amino-N-(4-amino-1-hydroxymethyl-butyl)-N-isobutyl-benzenesulfonamide → (1S,4S)-(1-{4-[(4-Amino-benzenesulfonyl)-isobutyl-amino]-5-hydroxy-pentylcarbamoyl}-2-naphthalen-1-yl-ethyl)-carbamic Acid Methyl Ester

HRID 987941Notes

Reaction equation

HRID 987941 reaction equation
[CH3:1][O:2][C:3]([NH:5][C@@H:6]([CH2:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1)[C:7]([OH:9])=O)=[O:4].[NH2:21][C:22]1[CH:27]=[CH:26][C:25]([S:28]([N:31]([C@H:36]([CH2:41][OH:42])[CH2:37][CH2:38][CH2:39][NH2:40])[CH2:32][CH:33]([CH3:35])[CH3:34])(=[O:30])=[O:29])=[CH:24][CH:23]=1>>[CH3:1][O:2][C:3](=[O:4])[NH:5][C@H:6]([C:7](=[O:9])[NH:40][CH2:39][CH2:38][CH2:37][C@H:36]([N:31]([S:28]([C:25]1[CH:24]=[CH:23][C:22]([NH2:21])=[CH:27][CH:26]=1)(=[O:30])=[O:29])[CH2:32][CH:33]([CH3:34])[CH3:35])[CH2:41][OH:42])[CH2:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1

Participants

3

Reactant 2

HCID 12986160(1S)-4-Amino-N-(4-amino-1-hydroxymethyl-butyl)-N-isobutyl-benzenesulfonamideHCID 12986162(2S)-2-methoxycarbonylamino-3-naphthalen-1-yl-propionic acid

Product 1

HCID 513924(1S,4S)-(1-{4-[(4-Amino-benzenesulfonyl)-isobutyl-amino]-5-hydroxy-pentylcarbamoyl}-2-naphthalen-1-yl-ethyl)-carbamic Acid Methyl Ester

Procedure

The title compound was prepared from general procedure A using (2S)-2-methoxycarbonylamino-3-naphthalen-1-yl-propionic acid and amine intermediate VII. The final product was obtained in 76% yield. Rf=0.57, EtOAc 100%.

Sources & evidence

ORD record
ord-c7f58c981ac946319b6c03b59409c41a
Source dataset
uspto-grants-2003_10
Patent number
US06632816B1

Reaction notes

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