HCID 178505054, compound → HCID 178505061, compound

HRID 272237Notes

Reaction equation

HRID 272237 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]([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)=[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]>[C:42]1([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[CH:43]=[CH:44][C:39]([C@H:36]2[CH2:37][CH2:38][C@H:33]([NH:8][CH2:9][C@H:10]([OH:32])[CH2:11][O:12][C:13]3[CH:14]=[CH:15][C:16]([OH:24])=[C:17]([NH:19][S:20]([CH3:23])(=[O:21])=[O:22])[CH:18]=3)[CH2:34][CH2:35]2)=[CH:40][CH:41]=1

Participants

4

Reactant 1

HCID 178505054HCID 178505054, compound

Product 1

HCID 178505061HCID 178505061, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 0.16 g of trans-N-[5-[((2S)-3-{benzyl[4-(1,1′-biphenyl-4-yl)cyclohexyl]amino}-2-hydroxypropyl)oxy]-2-(benzyloxy)phenyl]methanesulfonamide (0.23 mmol) and of 0.1 g of 10% palladium-on-charcoal (50% in water) in ethanol (6 ml) is placed under a hydrogen atmosphere and stirred for 4 hours. The reaction mixture is filtered through celite. The solvents are evaporated under reduced pressure and trans-N-{5-[((2S)-3-{[4-(1,1′-biphenyl-4-yl)cyclohexyl]amino}-2-hydroxypropyl)oxy]-2-hydroxyphenyl}methanesulfonamide is obtained in the form of a white solid (0.08 g, 68%) after purification on silica gel (eluent: dichloromethane/methanol, 99/1 to 85/15 gradient in 30 minutes).

Workup

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

Sources & evidence

ORD record
ord-17d2d21357364069aed33d0c1196c8ea
Source dataset
uspto-grants-2008_11
Patent number
US07453010B2

Reaction notes

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