Methanol → HCID 57473370, compound

HRID 523706Notes

Reaction equation

HRID 523706 reaction equation
C(O[C:6]([C:8]1[N:9]=[C:10]([CH3:26])[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[C:13]([O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:12]=2)=[O:7])CCC.[NH2:27][C@H:28]([C:30]([OH:32])=[O:31])[CH3:29].CO[Na].CO>>[OH:18][C:17]1[C:16]2[C:11](=[CH:12][C:13]([O:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[CH:14][CH:15]=2)[C:10]([CH3:26])=[N:9][C:8]=1[C:6]([NH:27][C@@H:28]([CH3:29])[C:30]([OH:32])=[O:31])=[O:7]

Participants

5

Reactant 4

HCID 887MethanolHCID 5950L-AlanineHCID 66713022HCID 66713022, compoundHCID 178418582HCID 178418582, compound

Product 1

HCID 57473370HCID 57473370, compoundYield 59%

Conditions

Temperature
120 °C

Procedure

A mixture of 4-Hydroxy-1-methyl-7-phenoxy-isoquinoline-3-carboxylic acid butyl ester (176 mg, 0.5 mmol), (S)-alanine (225 mg, 2.5 mmol) and a 0.5N solution of MeONa in MeOH (5 ml, 2.5 mmol) was heated in a microwave oven with stirring for 20 min at 120° C. before the mixture was concentrated in vacuo. To the residue was added water (15 ml) and the mixture was washed with Et2O (3×30 ml). The so purified aq. solution was acidified by the addition of 6N HCl and extracted with EtOAc (1×30 ml). The organic phase was dried over MgSO4 and concentrated in vacuo to give the title compound as a tan solid (108 mg); MS-(−)-ion M−1=365.1.

Workup

  1. concentrationwas concentrated in vacuo
  2. additionTo the residue was added water (15 ml)
  3. washthe mixture was washed with Et2O (3×30 ml)
  4. customThe so purified aq. solution
  5. additionwas acidified by the addition of 6N HCl
  6. extractionextracted with EtOAc (1×30 ml)
  7. dry with materialThe organic phase was dried over MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f639fc2f433942aaad95ef0b809a765a
Source dataset
uspto-grants-2016_05
Patent number
US09339527B2

Reaction notes

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