HCID 14357548, compound → HCID 14357550, compound

HRID 2165223Notes

Reaction equation

HRID 2165223 reaction equation
C(OC([NH:11][C@H:12]([C:23]([O:25][CH2:26][C@@H:27]([C:35]([O:37]CC1C=CC=CC=1)=[O:36])[NH:28][C:29](=[O:34])[C:30]([F:33])([F:32])[F:31])=[O:24])[C@@H:13]([CH3:22])[O:14]CC1C=CC=CC=1)=O)C1C=CC=CC=1.[H][H]>C(O)(=O)C.[Pd]>[NH2:11][C@H:12]([C:23]([O:25][CH2:26][C@@H:27]([C:35]([OH:37])=[O:36])[NH:28][C:29](=[O:34])[C:30]([F:33])([F:32])[F:31])=[O:24])[C@@H:13]([CH3:22])[OH:14]

Participants

5

Reactant 2

HCID 14357548HCID 14357548, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14357550HCID 14357550, compoundYield 93.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

Benzyl O-(N-benzyloxycarbonyl-O-benzyl-L-threonyl)-N-(trifluoroacetyl)-L-serinate (500 mg) was dissolved in acetic acid (10 ml) and the solution was hydrogenated over 10% palladium on activated carbon at 40 psi (500 mg) under 3 atomospheric pressure of hydrogen at room temperature for 1 hour. The mixture was filtered and the filtrate was evaporated to dryness. The residue was dissolved in a small amount of methanol and the solution was diluted with diethyl ether to give a white precipitate. The precipitate was crystallized from aqueous methanol to give 230 mg of pure O-(L-threonyl)-N-(trifluoroacetyl)-L-serine as a white powder.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated to dryness
  3. dissolutionThe residue was dissolved in a small amount of methanol
  4. additionthe solution was diluted with diethyl ether
  5. customto give a white precipitate
  6. customThe precipitate was crystallized from aqueous methanol

Sources & evidence

ORD record
ord-713cf9d9f2fd4febbcacf4b99be55382
Source dataset
uspto-grants-1990_07
Patent number
US04939241

Reaction notes

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