Acetic Acid → HCID 58941661, compound

HRID 1098310Notes

Reaction equation

HRID 1098310 reaction equation
C([O:8][C@H:9]([CH2:36][O:37]CC1C=CC=CC=1)[CH2:10][O:11][C:12](=[O:35])[NH:13][C:14]1[CH:23]=[C:22]2[C:17]([CH:18]=[C:19]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]([F:34])([F:33])[F:32])[NH:20][C:21]2=[O:24])=[CH:16][CH:15]=1)C1C=CC=CC=1.C(O)(=O)C>C(O)C.[OH-].[Pd+2].[OH-]>[OH:8][C@H:9]([CH2:36][OH:37])[CH2:10][O:11][C:12](=[O:35])[NH:13][C:14]1[CH:23]=[C:22]2[C:17]([CH:18]=[C:19]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]([F:32])([F:33])[F:34])[NH:20][C:21]2=[O:24])=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 58941660HCID 58941660, compound

Product 1

HCID 58941661HCID 58941661, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A mixture consisting of 26 mg (0.043 mmol) of (R)-2,3-bisbenzyloxypropyl[1-oxo-3-(2-trifluoromethylphenyl)-1,2-dihydroisoquinolin-7-yl]carbamate synthesized in Example 132; 5 mg (0.036 mmol) of palladium hydroxide; and 0.2 ml (3.49 mmol) of acetic acid, was suspended in 3 ml of ethanol, and the obtained suspension was then stirred under a hydrogen atmosphere for 2 hours. Thereafter, the reaction solution was filtrated with celite, and was then concentrated. The obtained residue was purified by silica gel chromatography (dichloromethane:methanol=10:1), so as to obtain 18 mg (100%) of (R)-2,3-dihydroxypropyl[1-oxo-3-(2-trifluoromethylphenyl)-1,2-dihydroisoquinolin-7-yl]carbamate in the form of a light yellow oily substance.

Workup

  1. filtrationThereafter, the reaction solution was filtrated with celite
  2. concentrationwas then concentrated
  3. customThe obtained residue was purified by silica gel chromatography (dichloromethane:methanol=10:1)

Sources & evidence

ORD record
ord-3137f7386256429db0a543f2a024cca3
Source dataset
uspto-grants-2012_03
Patent number
US08143274B2

Reaction notes

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