Ethanol → HCID 22175333, compound

HRID 1797751Notes

Reaction equation

HRID 1797751 reaction equation
[C:1]([O:5][C:6](=[O:33])[NH:7][CH2:8][C:9]1[N:10]([CH2:29][CH:30]([CH3:32])[CH3:31])[C:11](=[O:28])[C:12]2[C:17]([C:18]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[CH:16][C:15]([CH2:25][C:26]#N)=[CH:14][CH:13]=2)([CH3:4])([CH3:3])[CH3:2].[OH-:34].[K+].C(O)C.[OH-:39].[Na+]>>[C:1]([O:5][C:6]([NH:7][CH2:8][C:9]1[N:10]([CH2:29][CH:30]([CH3:31])[CH3:32])[C:11](=[O:28])[C:12]2[C:17]([C:18]=1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[CH:16][C:15]([CH2:25][C:26]([OH:39])=[O:34])=[CH:14][CH:13]=2)=[O:33])([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 4

HCID 702EthanolHCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 22175979HCID 22175979, compound

Product 1

HCID 22175333HCID 22175333, compoundYield 87%

Procedure

A mixture of tert-butyl[6-(cyanomethyl)-2-isobutyl-1-oxo-4-phenyl-1,2-dihydro-3-isoquinolinyl]methylcarbamate (0.13 g, 0.29 mmol), 2N potassium hydroxide solution (5 mL) and ethanol (5 mL) was refluxed for 4 h. The reaction mixture was diluted with 0.1N sodium hydroxide solution (100 mL) and washed with ethyl acetate (20 mL×2). The aqueous layer was separated, acidified with 1N hydrochloric acid and extracted with ethylacetate (100 mL×2). The organic layers were combined, washed with brine (20 mL), saturated aqueous sodium hydrogencarbonate (50 mL) and brine (50 mL), dried over, anhydrous magnesium sulfate and concentrated under reduced pressure to give (3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-1-oxo-4-phenyl-1,2-dihydroisoquinolin-6-yl)acetic acid (0.36 g, 87%) as a pale yellow oil.

Workup

  1. temperaturewas refluxed for 4 h
  2. washwashed with ethyl acetate (20 mL×2)
  3. customThe aqueous layer was separated
  4. extractionextracted with ethylacetate (100 mL×2)
  5. washwashed with brine (20 mL), saturated aqueous sodium hydrogencarbonate (50 mL) and brine (50 mL)
  6. dry with materialdried over, anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f962ee5e425b4d12913e179ceecda3b0
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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