methyl (2S)-2-amino-3-(4-phenylphenyl)propanoate hydrochloride → 3-[4-(3,4-Dichloro-benzyloxy)-phenyl]-2-oxo-1,2,3,5,7,8-hexahydro-4-oxa-1,6-diaza-anthracene-6-carboxylic acid isopropyl ester

HRID 39081Notes

Reaction equation

HRID 39081 reaction equation
[CH:1]([O:4][C:5]([N:7]1[CH:20](C(O)=O)[CH2:19][C:18]2[CH:17]=[C:16]3[C:11]([O:12][C@@H:13]([C:25]4[CH:30]=[CH:29][C:28]([O:31][CH2:32][C:33]5[CH:38]=[CH:37][C:36]([Cl:39])=[C:35]([Cl:40])[CH:34]=5)=[CH:27][CH:26]=4)[C:14](=[O:24])[NH:15]3)=[CH:10][C:9]=2[CH2:8]1)=[O:6])([CH3:3])[CH3:2].Cl.COC(=O)[C@@H](N)CC1C=CC(C2C=CC=CC=2)=CC=1>>[CH:1]([O:4][C:5]([N:7]1[CH2:20][CH2:19][C:18]2[CH:17]=[C:16]3[C:11]([O:12][CH:13]([C:25]4[CH:26]=[CH:27][C:28]([O:31][CH2:32][C:33]5[CH:38]=[CH:37][C:36]([Cl:39])=[C:35]([Cl:40])[CH:34]=5)=[CH:29][CH:30]=4)[C:14](=[O:24])[NH:15]3)=[CH:10][C:9]=2[CH2:8]1)=[O:6])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 45357110methyl (2S)-2-amino-3-(4-phenylphenyl)propanoate hydrochlorideHCID 66922756(S)-3-[4-(3,4-Dichloro-benzyloxy)-phenyl]-2-oxo-1,2,3,5,7,8-hexahydro-4-oxa-1,6-diaza-anthracene-6,7-dicarboxylic acid 6-isopropyl ester

Product 1

HCID 866440093-[4-(3,4-Dichloro-benzyloxy)-phenyl]-2-oxo-1,2,3,5,7,8-hexahydro-4-oxa-1,6-diaza-anthracene-6-carboxylic acid isopropyl esterYield 136.1%

Procedure

(S)-3-[4-(3,4-Dichloro-benzyloxy)-phenyl]-2-oxo-1,2,3,5,7,8-hexahydro-4-oxa-1,6-diaza-anthracene-6,7-dicarboxylic acid 6-isopropyl ester (120 mg) was coupled with (S)-2-amino-3-biphenyl-4-yl-propionic acid methyl ester hydrochloride according to general procedure A to provide (S)-74(S)-2-biphenyl-4-yl-1-methoxycarbonyl-ethylcarbamoyl)-3-[4-(3,4-dichloro-benzyloxy)-phenyl]-2-oxo-1,2,3,5,7,8-hexahydro-4-oxa-1,6-diaza-anthracene-6-carboxylic acid isopropyl ester (151 mg, LC/MS: m/z 825).

Sources & evidence

ORD record
ord-4e27105be9be46a4a50a25c462b53fb4
Source dataset
uspto-grants-2013_09
Patent number
US08524708B2

Reaction notes

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