Methanol → HCID 59370742, compound

HRID 1678715Notes

Reaction equation

HRID 1678715 reaction equation
C([N:8]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C@@H:19]([O:32][Si:33]([CH2:38][CH3:39])([CH2:36][CH3:37])[CH2:34][CH3:35])[CH2:20][N:21](CC2C=CC=CC=2)[CH2:22][CH2:23][OH:24])[CH:14]=1)[S:9]([CH3:12])(=[O:11])=[O:10])C1C=CC=CC=1.CO.O>C1COCC1.[OH-].[OH-].[Pd+2]>[OH:24][CH2:23][CH2:22][NH:21][CH2:20][C@@H:19]([C:15]1[CH:14]=[C:13]([NH:8][S:9]([CH3:12])(=[O:10])=[O:11])[CH:18]=[CH:17][CH:16]=1)[O:32][Si:33]([CH2:34][CH3:35])([CH2:36][CH3:37])[CH2:38][CH3:39]

Participants

6

Reactant 3

HCID 887MethanolHCID 962WaterHCID 59370749HCID 59370749, compound

Product 1

HCID 59370742HCID 59370742, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

(R)-N-benzyl-N-(3-(2-(benzyl-(2-hydroxyethyl)amino)-1-(triethylsilyloxy)ethyl)phenyl)methanesulfonamide (500 mg; an intermediate described in Reference Example 1 of WO 03/035620) was dissolved in THF (1.76 mL; manufactured by Wako Pure Chemical Industries, Ltd.) and methanol (1.76 mL; manufactured by Wako Pure Chemical Industries, Ltd.) under a nitrogen atmosphere, and 20% palladium hydroxide on carbon-49.94% wet with water (102.7 mg; manufactured by N.E. Chemcat Corp.) was added thereto. Subsequently, the reaction system was purged with hydrogen, and under a hydrogen atmosphere, the reaction solution was stirred for 15 hours at 50° C. The reaction solution was cooled to room temperature, purged with nitrogen, and then filtered. The filtrate was concentrated under reduced pressure, and thus the title compound (364 mg) was obtained.

Workup

  1. customSubsequently, the reaction system was purged with hydrogen
  2. temperatureThe reaction solution was cooled to room temperature
  3. custompurged with nitrogen
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-dc3dea8c466f4832beb04f0f53bb1050
Source dataset
uspto-grants-2011_08
Patent number
US08008506B2

Reaction notes

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