HCID 178504821, compound → HCID 178504824, compound

HRID 272248Notes

Reaction equation

HRID 272248 reaction equation
C([N:8]([CH2:31][C@H:32]([OH:53])[CH2:33][O:34][C:35]1[CH:40]=[CH:39][C:38]([O:41]CC2C=CC=CC=2)=[C:37]([S:49]([CH3:52])(=[O:51])=[O:50])[CH:36]=1)[C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]2[CH:30]=[CH:29][C:18]([C:19]([NH:21][NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[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]>[OH:53][C@H:32]([CH2:33][O:34][C:35]1[CH:40]=[CH:39][C:38]([OH:41])=[C:37]([S:49]([CH3:52])(=[O:51])=[O:50])[CH:36]=1)[CH2:31][NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]2[CH:30]=[CH:29][C:18]([C:19]([NH:21][NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:20])=[CH:17][CH:16]=2)[CH2:11][CH2:10]1

Participants

5

Reactant 1

HCID 178504821HCID 178504821, compound

Product 1

HCID 178504824HCID 178504824, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture or 0.166 g of trans-4-[4-(benzyl{(2S)-3-[4-(benzyloxy)-3-(methylsulfonyl)phenoxy]-2-hydroxypropyl}amino)cyclohexyl]-N′-phenylbenzohydrazide (0.226 mmol) and of 0.1 g of 10% palladium-on-charcoal (50% in water) in a mixture of ethanol (3.9 ml) and tetrahydrofuran (2.93 ml) is placed under hydrogen atmosphere and stirred for 48 h. 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 (0.02 g, 16%) 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-73a8f819c3d249baad01d3fbe525850e
Source dataset
uspto-grants-2008_11
Patent number
US07453010B2

Reaction notes

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