HCID 178504820, compound → HCID 178504823, compound

HRID 272250Notes

Reaction equation

HRID 272250 reaction equation
C([N:8]([CH2:32][C@H:33]([OH:54])[CH2:34][O:35][C:36]1[CH:41]=[CH:40][C:39]([O:42]CC2C=CC=CC=2)=[C:38]([S:50]([CH3:53])(=[O:52])=[O:51])[CH:37]=1)[C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]2[CH:31]=[CH:30][C:18]([C:19]([NH:21][CH2:22][C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)=[O:20])=[CH:17][CH:16]=2)[CH2:11][CH2:10]1)C1C=CC=CC=1>C(O)C.O1CCCC1.[Pd]>[F:29][C:26]1[CH:25]=[CH:24][C:23]([CH2:22][NH:21][C:19](=[O:20])[C:18]2[CH:17]=[CH:16][C:15]([C@H:12]3[CH2:11][CH2:10][C@H:9]([NH:8][CH2:32][C@H:33]([OH:54])[CH2:34][O:35][C:36]4[CH:41]=[CH:40][C:39]([OH:42])=[C:38]([S:50]([CH3:53])(=[O:52])=[O:51])[CH:37]=4)[CH2:14][CH2:13]3)=[CH:31][CH:30]=2)=[CH:28][CH:27]=1

Participants

5

Reactant 1

HCID 178504820HCID 178504820, compound

Product 1

HCID 178504823HCID 178504823, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 0.166 g of trans-4-[4-(benzyl{(2S)-3-[4-(benzyloxy)-3-(methylsulfonyl)phenoxy]-2-hydroxypropyl}amino)cyclohexyl]-N-(4-fluorobenzyl)benzamide (0.226 mmol) and of 0.117 g of 10% palladium-on-charcoal (50% in water) in a mixture of ethanol (5.3 ml) and tetrahydrofuran (4.02 ml) is placed under a hydrogen atmosphere and stirred for 48 hours. The catalyst is subsequently filtered off and the solvents are evaporated under reduced pressure. The title compound is obtained in the form of a white solid (0.92 g, 52%) after purification on silica gel (eluent: dichloromethane/methanol/aqueous ammonia 99/1/0.1 to 85/15/1.5 gradient in 30 min).

Workup

  1. filtrationThe catalyst is subsequently filtered off
  2. customthe solvents are evaporated under reduced pressure

Sources & evidence

ORD record
ord-e5024b9858cd47cf86be06251adde720
Source dataset
uspto-grants-2008_11
Patent number
US07453010B2

Reaction notes

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