Benzyl O-(O-benzyl-N-benzyloxycarbonyl-L-serinyl)-N-trifluoroacetyl-L-serinate → O-(L-serinyl)-N-trifluoroacetyl-L-serine

HRID 2165227Notes

Reaction equation

HRID 2165227 reaction equation
C([O:8][CH2:9][C@@H:10]([C:22]([O:24][CH2:25][C@@H:26]([C:34]([O:36]CC1C=CC=CC=1)=[O:35])[NH:27][C:28](=[O:33])[C:29]([F:32])([F:31])[F:30])=[O:23])[NH:11]C(OCC1C=CC=CC=1)=O)C1C=CC=CC=1>[Pd].C(O)(=O)C>[NH2:11][C@H:10]([C:22]([O:24][CH2:25][C@@H:26]([C:34]([OH:36])=[O:35])[NH:27][C:28](=[O:33])[C:29]([F:32])([F:31])[F:30])=[O:23])[CH2:9][OH:8]

Participants

4

Reactant 1

HCID 18639970Benzyl O-(O-benzyl-N-benzyloxycarbonyl-L-serinyl)-N-trifluoroacetyl-L-serinate

Product 1

HCID 18640004O-(L-serinyl)-N-trifluoroacetyl-L-serine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of benzyl O-(O-benzyl-N-benzyloxycarbonyl-L-serinyl)-N-trifluoroacetyl-L-serinate (1 g) and 10% palladium on activated carbon (1 g) in acetic acid (30 ml) was hydrogenated under hydrogen at 40 psi at room temperature for 6 hours. The reaction mixture was filtered with Celite (filter aid, trade mark, made by Nakarai Chemicals) and the filtrate was concentrated in vacuo and the residue was diluted with water (50 ml) and lyophylized to give O-(L-serinyl)-N-trifluoroacetyl-L-serine (430 ml).

Workup

  1. filtrationThe reaction mixture was filtered with Celite (filter aid, trade mark, made by Nakarai Chemicals)
  2. concentrationthe filtrate was concentrated in vacuo
  3. additionthe residue was diluted with water (50 ml)

Sources & evidence

ORD record
ord-d644a460fa7b466aabd2d7754067c494
Source dataset
uspto-grants-1990_07
Patent number
US04939241

Reaction notes

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