HCID 178472988, compound → HCID 178472990, compound

HRID 272240Notes

Reaction equation

HRID 272240 reaction equation
C([N:8]([CH2:28][C@H:29]([OH:51])[CH2:30][O:31][C:32]1[CH:37]=[CH:36][C:35]([O:38]CC2C=CC=CC=2)=[C:34]([NH:46][S:47]([CH3:50])(=[O:49])=[O:48])[CH:33]=1)[C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]2[CH:27]=[CH:26][C:18]([O:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:17][CH:16]=2)[CH2:11][CH2:10]1)C1C=CC=CC=1>C(O)C.[Pd]>[OH:51][C@H:29]([CH2:30][O:31][C:32]1[CH:37]=[CH:36][C:35]([OH:38])=[C:34]([NH:46][S:47]([CH3:50])(=[O:49])=[O:48])[CH:33]=1)[CH2:28][NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]2[CH:27]=[CH:26][C:18]([O:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:17][CH:16]=2)[CH2:11][CH2:10]1

Participants

4

Reactant 1

HCID 178472988HCID 178472988, compound

Product 1

HCID 178472990HCID 178472990, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of ethyl trans-(4-{4-[benzyl((2S)-3-{4-(benzyloxy)-3-[(methylsulfonyl)amino]phenoxy}-2-hydroxypropyl)amino]cyclohexyl}phenoxy)acetate (0.26 mmol) and of 0.25 g of 10% palladium-on-charcoal (50% in water) in ethanol (16 ml) is placed under hydrogen atmosphere and stirred for 7 h. The reaction mixture is filtered through celite. The solvents are evaporated under reduced pressure and ethyl trans-(4-{4-[((2S)-2-hydroxy-3-{4-hydroxy-3-[(methylsulfonyl)amino]phenoxy}propyl)amino]cyclohexyl}-phenoxy)acetate is obtained in the form of a white solid (0.08 g, 54%) after purification on silica gel (eluent: dichloromethane/methanol, 99/1 to 85/15 gradient in 30 min).

Workup

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

Sources & evidence

ORD record
ord-8c5639d77ada40dc9682185e441d5a69
Source dataset
uspto-grants-2008_11
Patent number
US07453010B2

Reaction notes

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