Methyl L-phenylalaninate hydrochloride → 1-Methylisoquinoline-3-carboxylic acid

HRID 1845012Notes

Reaction equation

HRID 1845012 reaction equation
CSC[CH2:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[C:7]([C:15]([OH:17])=[O:16])[N:6]=1.Cl.COC(=O)[C@H](CC1C=CC=CC=1)N>>[CH3:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[C:7]([C:15]([OH:17])=[O:16])[N:6]=1

Participants

3

Reactant 2

HCID 75736Methyl L-phenylalaninate hydrochlorideHCID 669404611-(2-Methylsulfanyl-ethyl)-isoquinoline-3-carboxylic acid

Product 1

HCID 189650101-Methylisoquinoline-3-carboxylic acidYield 11%

Procedure

0.25 g (11% overall yield) of 1-methyl-isoquinoline-3-carboxylic acid was synthesized according to the procedure described for the synthesis of 1-(2-methylsulfanyl-ethyl)-isoquinoline-3-carboxylic acid (in Example 298) starting from 2.20 g (10 mmol) of phenylalanine methyl ester hydrochloride. LCMS: 188 (M+1)+.

Sources & evidence

ORD record
ord-e8eee7a930494f2a80b641e70e5f02b2
Source dataset
uspto-grants-2015_02
Patent number
US08946259B2

Reaction notes

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