p-Toluenesulfonic acid monohydrate → HCID 18639975, compound

HRID 2165237Notes

Reaction equation

HRID 2165237 reaction equation
C([N:8]([C:41](=[O:46])[C:42]([F:45])([F:44])[F:43])[C@H:9]([C:38]([OH:40])=[O:39])[CH2:10][O:11][C:12](=[O:37])[CH:13]([NH:26]C(OCC1C=CC=CC=1)=O)[CH:14]([O:19]C1CCCCO1)[C:15]([F:18])([F:17])[F:16])C1C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[NH2:26][CH:13]([CH:14]([OH:19])[C:15]([F:16])([F:17])[F:18])[C:12]([O:11][CH2:10][C@@H:9]([C:38]([OH:40])=[O:39])[NH:8][C:41](=[O:46])[C:42]([F:44])([F:43])[F:45])=[O:37]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 18639966HCID 18639966, compound

Product 1

HCID 18639975HCID 18639975, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of benzyl N-trifluoroacetyl-O-[2-benzyloxycarbonylamino-3-(2-tetrahydropyranyloxy)-4,4,4-trifluoro-1-oxobutyl]-L-serine (1.36 g) and p-toluenesulfonic acid monohydrate (39 mg) in methanol (14 ml) was stirred overnight. The solvent was distilled off and the residue was diluted with ethyl acetate and washed successively with 10% aqueous sodium hydrogen carbonate and brine. After drying over sodium sulfate, the ethyl acetate extract was filtered and concentrated. The residue was dissolved in acetic acid (50 ml) and 10% palladium on activated carbon (500 mg) was added. The mixture was hydrogenated under hydrogen at 40 psi at room temperature for an hour. The solvent was distilled off and the residue was lyophilized to give O-(2-amino-3-hydroxy-4,4,4-trifluoro-1-oxobutyl)-N-trifluoroacetyl-L-serine (685 mg).

Workup

  1. distillationThe solvent was distilled off
  2. additionthe residue was diluted with ethyl acetate
  3. washwashed successively with 10% aqueous sodium hydrogen carbonate and brine
  4. dry with materialAfter drying over sodium sulfate
  5. extractionthe ethyl acetate extract
  6. filtrationwas filtered
  7. concentrationconcentrated
  8. dissolutionThe residue was dissolved in acetic acid (50 ml)
  9. addition10% palladium on activated carbon (500 mg) was added
  10. waitThe mixture was hydrogenated under hydrogen at 40 psi at room temperature for an hour
  11. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-b25de2035a9945f59da0be3b37f2efc7
Source dataset
uspto-grants-1990_07
Patent number
US04939241

Reaction notes

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