HCID 178505059, compound → HCID 178505065, compound

HRID 272242Notes

Reaction equation

HRID 272242 reaction equation
C([N:8]([CH2:26][C@H:27]([OH:49])[CH2:28][O:29][C:30]1[CH:35]=[CH:34][C:33]([O:36]CC2C=CC=CC=2)=[C:32]([NH:44][S:45]([CH3:48])(=[O:47])=[O:46])[CH:31]=1)[C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]2[CH:25]=[CH:24][C:18]([O:19][CH2:20][C:21]([OH:23])=[O:22])=[CH:17][CH:16]=2)[CH2:11][CH2:10]1)C1C=CC=CC=1>O1CCCC1.C(O)C.[Pd]>[OH:49][C@H:27]([CH2:28][O:29][C:30]1[CH:35]=[CH:34][C:33]([OH:36])=[C:32]([NH:44][S:45]([CH3:48])(=[O:47])=[O:46])[CH:31]=1)[CH2:26][NH:8][C@H:9]1[CH2:10][CH2:11][C@H:12]([C:15]2[CH:16]=[CH:17][C:18]([O:19][CH2:20][C:21]([OH:23])=[O:22])=[CH:24][CH:25]=2)[CH2:13][CH2:14]1

Participants

5

Reactant 1

HCID 178505059HCID 178505059, compound

Product 1

HCID 178505065HCID 178505065, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 0.3 g of trans-(4-{4-[benzyl((2S)-3-{4-(benzyloxy)-3-[(methylsulfonyl)amino]phenoxy}-2-hydroxypropyl)amino]cyclohexyl}phenoxy)acetic acid (0.44 mmol) and of 0.20 g of 10% palladium-on-charcoal (50% in water) in a mixture of tetrahydrofuran (5 ml) and ethanol (5 ml) is placed under a hydrogen atmosphere and stirred for 4 h. The reaction mixture is filtered through celite. The solvents are evaporated under reduced pressure and trans-(4-{4-[((2S)-2-hydroxy-3-{4-hydroxy-3-[(methylsulfonyl)amino]phenoxy}propyl)amino]cyclohexyl}-phenoxy)acetic acid is obtained in the form of a white solid (0.07 g, 32%) after purification on C18-grafted silica (eluent: water/acetonitrile, 95/5 to 5/95 gradient in 15 min).

Workup

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

Sources & evidence

ORD record
ord-598d06d1d3c942319474c69f5b08fc03
Source dataset
uspto-grants-2008_11
Patent number
US07453010B2

Reaction notes

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