Potassium Hydroxide → HCID 11442088, compound

HRID 908833Notes

Reaction equation

HRID 908833 reaction equation
C([O:8][C:9](=[O:40])[CH2:10][NH:11][C:12]([C:14]1[N:15]=[C:16]([CH3:39])[C:17]2[C:22]([C:23]=1[O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[CH:21][CH:20]=[C:19]([O:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH:18]=2)=[O:13])C1C=CC=CC=1.[OH-].[K+]>CCO>[CH2:25]([O:24][C:23]1[C:22]2[C:17](=[CH:18][C:19]([O:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[CH:20][CH:21]=2)[C:16]([CH3:39])=[N:15][C:14]=1[C:12]([NH:11][CH2:10][C:9]([OH:40])=[O:8])=[O:13])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 66712846HCID 66712846, compound

Product 1

HCID 11442088HCID 11442088, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of [(4-benzyloxy-1-methyl-7-phenoxy-isoquinoline-3-carbonyl)-amino]-acetic acid benzyl ester (160 mg, 0.3 mmol; Example D-81 d), KOH (325 mg, 5 mmol) and EtOH (10 ml) was stirred at ambient temperature for 18 h before the solvent was evaporated in vacuo. To the residue was added water (5 ml) and the mixture was washed with Et2O (2×20 ml). Then the solution was acidified by addition of aqueous 6N HCl and extracted with EtOAc (2×20 ml). The combined organic phases were dried over MgSO4 and concentrated in vacuo to give the title compound as a tan gum (93 mg); MS-(+)-ion: M+1=443.0.

Workup

  1. customwas evaporated in vacuo
  2. additionTo the residue was added water (5 ml)
  3. washthe mixture was washed with Et2O (2×20 ml)
  4. additionThen the solution was acidified by addition of aqueous 6N HCl
  5. extractionextracted with EtOAc (2×20 ml)
  6. dry with materialThe combined organic phases were dried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ef2662526bb746638d71cc355e7793b1
Source dataset
uspto-grants-2011_09
Patent number
US08017625B2

Reaction notes

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