Alanine methyl ester hydrochloride → (S)-2-[(7-Isopropoxy-1-chloro-4-hydroxy-isoquinoline-3-carbonyl)-amino]-propionic acid

HRID 250319Notes

Reaction equation

HRID 250319 reaction equation
[CH:1]([O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([OH:19])=[C:10]([C:16]([OH:18])=O)[N:11]=[C:12]2[Cl:15])=[CH:7][CH:6]=1)([CH3:3])[CH3:2].Cl.C[O:22][C:23](=[O:27])[C@H:24]([CH3:26])[NH2:25]>>[CH:1]([O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([OH:19])=[C:10]([C:16]([NH:25][C@@H:24]([CH3:26])[C:23]([OH:27])=[O:22])=[O:18])[N:11]=[C:12]2[Cl:15])=[CH:7][CH:6]=1)([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 2733257Alanine methyl ester hydrochlorideHCID 538704391-Chloro-4-hydroxy-7-isopropoxy-isoquinoline-3-carboxylic acid

Product 1

HCID 86761022(S)-2-[(7-Isopropoxy-1-chloro-4-hydroxy-isoquinoline-3-carbonyl)-amino]-propionic acid

Procedure

Analogously to Example A-56, 0.040 g of 7-isopropoxy-1-chloro-4-hydroxy-isoquinoline-3-carboxylic acid were allowed to react with 0.020 g of L-Alanine methyl ester hydrochloride to give, after hydrolysis of the intermediate ester, 0.047 g of a white solid: MS-(−)-ion, M−1=353.1 amu.

Workup

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Sources & evidence

ORD record
ord-75c246fbc50d452eaed44f130d284fe9
Source dataset
uspto-grants-2011_01
Patent number
US07863292B2

Reaction notes

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