HCID 178454211, compound → HCID 178454210, compound

HRID 591292Notes

Reaction equation

HRID 591292 reaction equation
C([O:8][C@H:9]1[CH2:12][C@H:11]([O:13][C:14]2[CH:45]=[CH:44][C:17]([CH2:18][C@H:19]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:20][C@@H:21]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[CH:16][CH:15]=2)[CH2:10]1)C1C=CC=CC=1>CO.[Pd]>[OH:8][C@H:9]1[CH2:10][C@H:11]([O:13][C:14]2[CH:15]=[CH:16][C:17]([CH2:18][C@H:19]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:20][C@@H:21]([C:30]([O:32][C:33]([CH3:34])([CH3:35])[CH3:36])=[O:31])[NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[CH:44][CH:45]=2)[CH2:12]1

Participants

4

Reactant 1

HCID 178454211HCID 178454211, compound

Product 1

HCID 178454210HCID 178454210, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 23938PalladiumSolvent

Procedure

43 mg (0.07 mmol) of di-tert-butyl (4S)-4-(4-{trans-[3-(benzyloxy)cyclobutyl]oxy}benzyl)-N-(tert-butoxycarbonyl)-L-glutamate were dissolved in 10 mL of methanol and under argon atmosphere palladium (10% on charcoal) was added and the suspension hydrogenated overnight at room temperature. The reaction mixture was filtered, the solvent evaporated and the residue was chromatographed on silica gel using a hexane/ethyl acetate gradient, and the appropriate fractions were combined and concentrated.

Workup

  1. additionwas added
  2. customthe suspension hydrogenated overnight
  3. customat room temperature
  4. filtrationThe reaction mixture was filtered
  5. customthe solvent evaporated
  6. customthe residue was chromatographed on silica gel using a hexane/ethyl acetate gradient
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e73c585f217f4f61a95e90b2c337ea0a
Source dataset
uspto-grants-2016_01
Patent number
US09238631B2

Reaction notes

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