HCID 178505056, compound → HCID 178505063, compound

HRID 272246Notes

Reaction equation

HRID 272246 reaction equation
C([N:8]([CH2:35][C@H:36]([OH:58])[CH2:37][O:38][C:39]1[CH:44]=[CH:43][C:42]([O:45]CC2C=CC=CC=2)=[C:41]([NH:53][S:54]([CH3:57])(=[O:56])=[O:55])[CH:40]=1)[C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]2[CH:34]=[CH:33][C:18]([C:19]([NH:21][C@H:22]([C:30]([OH:32])=[O:31])[CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:20])=[CH:17][CH:16]=2)[CH2:11][CH2:10]1)C1C=CC=CC=1>C(O)C.[Pd]>[OH:58][C@H:36]([CH2:37][O:38][C:39]1[CH:44]=[CH:43][C:42]([OH:45])=[C:41]([NH:53][S:54]([CH3:57])(=[O:56])=[O:55])[CH:40]=1)[CH2:35][NH:8][C@H:9]1[CH2:10][CH2:11][C@H:12]([C:15]2[CH:34]=[CH:33][C:18]([C:19]([NH:21][C@H:22]([C:30]([OH:32])=[O:31])[CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:20])=[CH:17][CH:16]=2)[CH2:13][CH2:14]1

Participants

4

Reactant 1

HCID 178505056HCID 178505056, compound

Product 1

HCID 178505063HCID 178505063, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 0.2 g of trans-N-(4-{4-[benzyl((2S)-3-{4-(benzyloxy)-3-[(methylsulfonyl)-amino]phenoxy}-2-hydroxypropyl)amino]cyclohexyl}-benzoyl)-L-phenylalanine (0.248 mmol) and of 0.1 g of 10% palladium-on-charcoal (50% in water) in ethanol (15 ml) is placed under hydrogen atmosphere and stirred for 3 h. The reaction mixture is filtered through celite. The solvents are evaporated under reduced pressure and trans-N-(4-{4-[((2S)-2-hydroxy-3-{4-hydroxy-3-[(methylsulfonyl)amino]phenoxy}propyl)amino]cyclohexyl}benzoyl)-L-phenylalanine is obtained in the form of a white solid (0.049 g, 31%) 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-bfa673e905e14cf687d7a51243da65ad
Source dataset
uspto-grants-2008_11
Patent number
US07453010B2

Reaction notes

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