Ethyl Acetate → [(4-Hydroxy-1-methoxymethyl-isoquinoline-3-carbonyl)-amino]-acetic acid

HRID 250450Notes

Reaction equation

HRID 250450 reaction equation
C([O:8][C:9](=[O:35])[CH2:10][NH:11][C:12]([C:14]1[N:15]=[C:16]([CH2:32][O:33][CH3:34])[C:17]2[C:22]([C:23]=1[O:24]CC1C=CC=CC=1)=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:13])C1C=CC=CC=1.CCOC(C)=O>[Pd].CO>[OH:24][C:23]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([CH2:32][O:33][CH3:34])=[N:15][C:14]=1[C:12]([NH:11][CH2:10][C:9]([OH:35])=[O:8])=[O:13]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 66712976[(4-Benzyloxy-1-methoxymethyl-isoquinoline-3-carbonyl)-amino]-acetic acid benzyl ester

Product 1

HCID 11471810[(4-Hydroxy-1-methoxymethyl-isoquinoline-3-carbonyl)-amino]-acetic acidYield 89.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of [(4-benzyloxy-1-methoxymethyl-isoquinoline-3-carbonyl)-amino]-acetic acid benzyl ester (134 mg, 0.285 mmol), Pd/C (100 mg, 10 wt % Pd), EtOAc (10 ml) and MeOH (50 ml) was stirred under a H2-atmosphere at ambient pressure and temperature for 18 h. Then the mixture was filtered through a pad of celite. Celite and filter cake were washed thoroughly with EtOAc and the combined organic phases were concentrated in vacuo to give the title compound as a tan solid (74 mg); MS-(−)-ion: M−1=289.2.

Workup

  1. filtrationThen the mixture was filtered through a pad of celite
  2. filtrationCelite and filter cake
  3. washwere washed thoroughly with EtOAc
  4. concentrationthe combined organic phases were concentrated in vacuo

Sources & evidence

ORD record
ord-a094aff7cf6b46e8953c772728726a8b
Source dataset
uspto-grants-2011_01
Patent number
US07863292B2

Reaction notes

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