HCID 178472569, compound → HCID 178472570, compound

HRID 272243Notes

Reaction equation

HRID 272243 reaction equation
C([N:8]([CH2:33][C@H:34]([OH:56])[CH2:35][O:36][C:37]1[CH:42]=[CH:41][C:40]([O:43]CC2C=CC=CC=2)=[C:39]([NH:51][S:52]([CH3:55])(=[O:54])=[O:53])[CH:38]=1)[C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]2[CH:32]=[CH:31][C:18]([C:19]([NH:21][C@@H:22]([CH:28]([CH3:30])[CH3:29])[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[O:20])=[CH:17][CH:16]=2)[CH2:11][CH2:10]1)C1C=CC=CC=1>C(O)C.[Pd]>[OH:56][C@H:34]([CH2:35][O:36][C:37]1[CH:42]=[CH:41][C:40]([OH:43])=[C:39]([NH:51][S:52]([CH3:55])(=[O:54])=[O:53])[CH:38]=1)[CH2:33][NH:8][C@H:9]1[CH2:10][CH2:11][C@H:12]([C:15]2[CH:32]=[CH:31][C:18]([C:19]([NH:21][C@H:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:28]([CH3:30])[CH3:29])=[O:20])=[CH:17][CH:16]=2)[CH2:13][CH2:14]1

Participants

4

Reactant 1

HCID 178472569HCID 178472569, compound

Product 1

HCID 178472570HCID 178472570, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 1.35 g (0.35 mmol) of ethyl trans-(2S)-2-[(4-{4-[benzyl((2S)-3-{4-(benzyloxy)-3-[(methylsulfonyl)amino]phenoxy}-2-hydroxypropyl)amino]cyclohexyl}benzoyl)amino]-3-methylbutanoate and of 0.177 g of palladium-on-charcoal (10% Pd, 50% in water) in 15 ml of ethanol is placed under hydrogen atmosphere and stirred for 3 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 (0.138 g, 44%) 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-930f5551543244cb994021cd2b23ef3c
Source dataset
uspto-grants-2008_11
Patent number
US07453010B2

Reaction notes

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