L-Alanine → 2-(S)-[(4-Hydroxy-7-phenylsulfanyl-isoquinoline-3-carbonyl)-amino]-propionic acid

HRID 250331Notes

Reaction equation

HRID 250331 reaction equation
C(O[C:6]([C:8]1[N:9]=[CH:10][C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[C:13]([S:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:12]=2)=[O:7])CCC.[NH2:26][C@H:27]([C:29]([OH:31])=[O:30])[CH3:28]>C[O-].[Na+].CO>[OH:18][C:17]1[C:16]2[C:11](=[CH:12][C:13]([S:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[CH:14][CH:15]=2)[CH:10]=[N:9][C:8]=1[C:6]([NH:26][C@@H:27]([CH3:28])[C:29]([OH:31])=[O:30])=[O:7]

Participants

4

Reactant 2

HCID 5950L-AlanineHCID 667130924-Hydroxy-7-phenylsulfanyl-isoquinoline-3-carboxylic acid butyl ester

Product 1

HCID 248617402-(S)-[(4-Hydroxy-7-phenylsulfanyl-isoquinoline-3-carbonyl)-amino]-propionic acidYield 72%

Reagents, catalysts & solvents 1

HCID 23694274Sodium methanolate methanolSolvent

Procedure

A mixture of 4-hydroxy-7-phenylsulfanyl-isoquinoline-3-carboxylic acid butyl ester (0.20 g) and L-alanine (0.75 g) in 0.5 M NaOMe/MeOH (11.3 ml) was heated to reflux for 36 h. After cooling, reaction mixture was concentrated. The residue was suspended in water (50 ml) and extracted with ethyl acetate (50 ml) which was discarded. The aqueous layer was acidified by 2 N HCl aqueous solution. Extracted with ethyl acetate (2×50 ml). Combined organic layers were dried over magnesium sulfate, filtered, and concentrated to give the title compound (0.15 g). MS-(−)-ion: M−1=367.1.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 36 h
  3. temperatureAfter cooling
  4. customreaction mixture
  5. concentrationwas concentrated
  6. extractionextracted with ethyl acetate (50 ml) which
  7. extractionExtracted with ethyl acetate (2×50 ml)
  8. dry with materialCombined organic layers were dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-33eeda3e99a348778876622894aff96f
Source dataset
uspto-grants-2011_01
Patent number
US07863292B2

Reaction notes

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