HCID 178505058, compound → HCID 178505064, compound

HRID 272239Notes

Reaction equation

HRID 272239 reaction equation
C([N:8]([C@H:33]1[CH2:38][CH2:37][C@H:36]([C:39]2[CH:44]=[CH:43][C:42]([OH:45])=[CH:41][CH:40]=2)[CH2:35][CH2:34]1)[CH2:9][C@H:10]([OH:32])[CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([O:24]CC2C=CC=CC=2)=[C:17]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])[CH:18]=1)C1C=CC=CC=1>C(O)C.[Pd]>[OH:24][C:16]1[CH:15]=[CH:14][C:13]([O:12][CH2:11][C@@H:10]([OH:32])[CH2:9][NH:8][C@H:33]2[CH2:38][CH2:37][C@H:36]([C:39]3[CH:44]=[CH:43][C:42]([OH:45])=[CH:41][CH:40]=3)[CH2:35][CH2:34]2)=[CH:18][C:17]=1[NH:19][S:20]([CH3:23])(=[O:22])=[O:21]

Participants

4

Reactant 1

HCID 178505058HCID 178505058, compound

Product 1

HCID 178505064HCID 178505064, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 0.8 g (1.26 mmol) of trans-N-[5-[((2S)-3-{benzyl[4-(4-hydroxyphenyl)cyclohexyl]amino}-2-hydroxypropyl)oxy]-2-(benzyloxy)phenyl]methanesulfonamide and of 0.2 g of 10% palladium-on-charcoal (50% in water) in ethanol (40 ml) is placed under hydrogen atmosphere and stirred for 2 h. The reaction mixture is filtered through celite. The solvents are evaporated under reduced pressure and trans-N-{2-hydroxy-5-[((2S)-2-hydroxy-3-{[4-(4-hydroxyphenyl)cyclohexyl]amino}propyl)oxy]phenyl}methanesulfonamide is obtained in the form of a white solid (0.24 g, 67%) after purification on silica gel (eluent: dichloromethane/methanol, 95/5 to 80/20 gradient in 15 min).

Workup

  1. filtrationThe reaction mixture is filtered through celite
  2. customThe solvents are evaporated under reduced pressure

Sources & evidence

ORD record
ord-6ef8d563c4714e529368a1d32d1aff07
Source dataset
uspto-grants-2008_11
Patent number
US07453010B2

Reaction notes

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