HCID 54514706, compound → HCID 18639997, compound

HRID 2165225Notes

Reaction equation

HRID 2165225 reaction equation
C(OC([NH:11][CH:12]([C:21]([O:23][CH2:24][C@@H:25]([C:33]([O:35]CC1C=CC=CC=1)=[O:34])[NH:26][C:27](=[O:32])[C:28]([F:31])([F:30])[F:29])=[O:22])[CH:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[OH:14])=O)C1C=CC=CC=1>[Pd].C(O)(=O)C>[C:15]1([CH:13]([OH:14])[CH:12]([C:21]([O:23][CH2:24][C@@H:25]([C:33]([OH:35])=[O:34])[NH:26][C:27](=[O:32])[C:28]([F:29])([F:30])[F:31])=[O:22])[NH2:11])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 1

HCID 54514706HCID 54514706, compound

Product 1

HCID 18639997HCID 18639997, compoundYield 74.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of benzyl O-(N-benzyloxycarbonyl-3-phenyl-D,L-serinyl)-N-trifluoroacetyl-L-serinate (324 mg) and 10% palladium on activated carbon (400 mg) in acetic acid (5 ml) was hydrogenated at 40 psi under hydrogen at room temperature for 2 hours. The reaction mixture was filtered with Celite (filter aid, trade mark, made by Nakarai Chemicals) and concentrated and lyophilized to give O-(3-phenyl-D,L-serinyl)-N-trifluoroacetyl-L-serine (150 mg).

Workup

  1. filtrationThe reaction mixture was filtered with Celite (filter aid, trade mark, made by Nakarai Chemicals)
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-0401dfd1d26849db868c99b77eab081e
Source dataset
uspto-grants-1990_07
Patent number
US04939241

Reaction notes

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