HCID 11760406, compound → HCID 14523456, compound

HRID 2288905Notes

Reaction equation

HRID 2288905 reaction equation
C([NH:11][C@H:12]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(OCC1C=CC=CC=1)=O.[H][H]>C(O)C.C(OCC)(=O)C.[Pd]>[NH2:11][C@H:12]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 2

HCID 11760406HCID 11760406, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 14523456HCID 14523456, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (N-carbobenzyloxy)-(L)-homophenylalanine, tert-butyl ester (100 mg, 0.281 mmol) in anhydrous ethanol (2 mL) and anhydrous ethyl acetate (2 mL) was degassed and the reaction flask filled with hydrogen. 10% Palladium on carbon catalyst (25 mg) was added and the mixture was hydrogenated under a balloon of hydrogen at room temperature for 2.3 hr. The catalyst was removed by filtration through a pad of celite, and solvent was removed from the filtrate by rotoevaporation. After pumping under reduced pressure at room temperature, the material thus obtained (homogeneous by TLC in 4/1 hexane/ethyl acetate) was used in the subsequent reaction without further purification.

Workup

  1. customThe catalyst was removed by filtration through a pad of celite, and solvent
  2. customwas removed from the filtrate by rotoevaporation
  3. customAfter pumping under reduced pressure at room temperature
  4. customthe material thus obtained (homogeneous by TLC in 4/1 hexane/ethyl acetate)
  5. customwas used in the subsequent reaction without further purification

Sources & evidence

ORD record
ord-bebb3eb5e4d149579e08b63b20cf04bd
Source dataset
uspto-grants-2000_07
Patent number
US06090841

Reaction notes

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