methyl D-alaninate → (R)-2-[(7-Benzyloxy-1-chloro-4-hydroxy-isoquinoline-3-carbonyl)-amino]-propionic acid methyl ester

HRID 523660Notes

Reaction equation

HRID 523660 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([OH:23])=[C:14]([C:20](O)=[O:21])[N:15]=[C:16]2[Cl:19])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:24][O:25][C:26](=[O:30])[C@@H:27]([CH3:29])[NH2:28]>>[CH3:24][O:25][C:26](=[O:30])[C@H:27]([NH:28][C:20]([C:14]1[N:15]=[C:16]([Cl:19])[C:17]2[C:12]([C:13]=1[OH:23])=[CH:11][CH:10]=[C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH:18]=2)=[O:21])[CH3:29]

Participants

3

Reactant 2

HCID 89020methyl D-alaninateHCID 186981307-Benzyloxy-1-chloro-4-hydroxy-isoquinoline-3-carboxylic acid

Product 1

HCID 86595455(R)-2-[(7-Benzyloxy-1-chloro-4-hydroxy-isoquinoline-3-carbonyl)-amino]-propionic acid methyl ester

Procedure

7-Benzyloxy-1-chloro-4-hydroxy-isoquinoline-3-carboxylic acid, 0.33 g, was coupled with D-Alanine methyl ester analogously to Example A-1 a). 0.246 g of off-white solid were obtained: MS-(+)-ion, M+1=415.0 amu.

Sources & evidence

ORD record
ord-d71c72ae4cfa4195a6bce5379a22cd1d
Source dataset
uspto-grants-2016_05
Patent number
US09339527B2

Reaction notes

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