HCID 13727808, compound → HCID 13727773, compound

HRID 652354Notes

Reaction equation

HRID 652354 reaction equation
C1(COC([NH:11][C@H:12]([C:17]([O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])=[O:18])[CH2:13][CH:14]([CH3:16])[CH3:15])=O)C=CC=CC=1.[H][H]>C(OCC)(=O)C.[Pd]>[NH2:11][C@H:12]([C:17]([O:19][CH2:20][CH2:21][Si:22]([CH3:23])([CH3:25])[CH3:24])=[O:18])[CH2:13][CH:14]([CH3:16])[CH3:15]

Participants

5

Reactant 2

HCID 13727808HCID 13727808, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13727773HCID 13727773, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 9.1 g (24.9 mmol) of [(phenylmethoxy)carbonyl]-L-leucine, 2-(trimethylsilyl)ethyl ester in 200 ml of ethyl acetate cooled in an ice bath under nitrogen was added 1 g of 10% palladium on charcoal. The reaction mixture was subjected to a steady stream of hydrogen for 21/2 hours at room temperature, then filtered and concentrated in vacuo to remove volatiles. The liquid product obtained was homogeneous by TLC. The yield was 5.8 g and the free amino-ester was used directly without further characterization.

Workup

  1. custom2 hours
  2. customat room temperature
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto remove volatiles
  6. customThe liquid product obtained

Sources & evidence

ORD record
ord-ddf954c3a779411d8de11937f7cbfed7
Source dataset
uspto-grants-1987_06
Patent number
US04670541

Reaction notes

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