HCID 13727808, compound → HCID 13727773, compound

HRID 1249303Notes

Reaction equation

HRID 1249303 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]>[Pd].C(OCC)(=O)C>[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

1 g. of 10% palladium on carbon catalyst is added to a solution of [(phenylmethoxy)carbonyl]-L-leucine, 2-(trimethylsilyl)ethyl ester (9.1 g., 24.9 mmole) in ethyl acetate (200 ml.) cooled in an ice-bath under nitrogen. The reaction mixture is subjected to a steady stream of hydrogen gas for 2.5 hours at room temperature, then filtered and concentrated in vacuo to remove volatiles and yield 5.8 g. of L-leucine, 2-(trimethylsilyl)-ethyl ester as a liquid product. TLC (silica gel, 3:1 hexane:ethyl acetate) Rf =0.08.

Workup

  1. temperaturecooled in an ice-bath under nitrogen
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customto remove volatiles and yield 5.8 g

Sources & evidence

ORD record
ord-85491b51461c4319b8fdfcebc7769aba
Source dataset
uspto-grants-1986_12
Patent number
US04629724

Reaction notes

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