Methanol → HCID 59370742, compound

HRID 1873961Notes

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.[H][H]>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

Conditions

Temperature: 50 °C

Procedure

(R)—N-Benzyl-N-(3-(2-(benzyl(2-hydroxyethyl)amino)-1-(triethylsilyloxy)ethyl)phenyl)methanesulfonamide (500 mg; intermediate described in Reference example 1 of International Publication No. WO03/035620) 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 nitrogen atmosphere, and added with 20% palladium hydroxide on carbon-49.94% wet with Water (102.7 mg; manufactured by N. E. Chemcat Corp.). The reaction system was replaced with hydrogen, and stirred at 50° C. for 15 hours under hydrogen atmosphere. After cooling the reaction solution to room temperature and replacement with nitrogen, filtration was carried out. The filtrate was concentrated under reduced pressure to obtain the title compound (364 mg).

Workup

temperatureAfter cooling the reaction solution to room temperature
filtrationreplacement with nitrogen, filtration
concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record: ord-c7994e82160a4ab39c5a2e0952238536
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08304443B2

Reaction notes

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