benzyl trifluoroacetyl-L-serinate → benzyl O-[3(R)-acetoxy-2(S)-benzyloxycarbonylamino-1-oxobutyl]-N-trifluoroacetyl-L-serinate

HRID 2165233Notes

Reaction equation

HRID 2165233 reaction equation
[C:1]([O:4][C@H:5]([CH3:21])[C@@H:6]([C:18]([OH:20])=[O:19])[NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])(=[O:3])[CH3:2].[F:22][C:23]([F:41])([F:40])[C:24]([NH:26][C@H:27]([C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31])[CH2:28]O)=[O:25]>C(Cl)Cl>[C:1]([O:4][C@H:5]([CH3:21])[C@H:6]([NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[C:18]([O:20][CH2:28][C@@H:27]([C:30]([O:32][CH2:33][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)=[O:31])[NH:26][C:24](=[O:25])[C:23]([F:22])([F:40])[F:41])=[O:19])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 14357546benzyl trifluoroacetyl-L-serinateHCID 18640002O-acetyl-N-benzyloxycarbonyl-L-threonine

Product 1

HCID 18639967benzyl O-[3(R)-acetoxy-2(S)-benzyloxycarbonylamino-1-oxobutyl]-N-trifluoroacetyl-L-serinateYield 73.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of O-acetyl-N-benzyloxycarbonyl-L-threonine (1 g) and benzyl N-trifluoroacetyl-L-serinate (987 mg) in methylene chloride (20 ml) was added N,N-diethylaminopropyl-N'-ethylcarbodiimide hydrochloride (1.22 g) and 4-N,N-dimethylaminopyridine (77.8 mg) at room temperature. After stirring for an hour at room temperature, the reaction mixture was washed successively with aqueous hydrogen chloride, water, 10% aqueous sodium hydrogen carbonate and brine. After drying over sodium sulfate, the methylene chloride extract was filtered and concentrated. The residue was chromatographed on silica gel (20 g) eluting successively with a mixture of hexane and methylene chloride (1:1), methylene chloride and a mixture of methylene chloride and acetone (125:1) to give benzyl O-[3(R)-acetoxy-2(S)-benzyloxycarbonylamino-1-oxo-butyl]-N-trifluoroacetyl-L-serinate (1.42 g).

Workup

  1. washthe reaction mixture was washed successively with aqueous hydrogen chloride, water, 10% aqueous sodium hydrogen carbonate and brine
  2. dry with materialAfter drying over sodium sulfate
  3. extractionthe methylene chloride extract
  4. filtrationwas filtered
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel (20 g)
  7. washeluting successively with a mixture of hexane and methylene chloride (1:1), methylene chloride
  8. additiona mixture of methylene chloride and acetone (125:1)

Sources & evidence

ORD record
ord-1059afd4609c49ac9334cb5a4acaa2ca
Source dataset
uspto-grants-1990_07
Patent number
US04939241

Reaction notes

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