p-Toluenesulfonic acid monohydrate → (2S,3S)-2-(tert-Butoxycarbonylamino)-3-(benzyloxy)-4,4,4-trifluoro-1-butanol

HRID 238574Notes

Reaction equation

HRID 238574 reaction equation
[CH2:1]([O:8][C@H:9]([C@@H:14]1[CH2:18][O:17]C(C)(C)[N:15]1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:10]([F:13])([F:12])[F:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH2:1]([O:8][C@H:9]([C:10]([F:11])([F:13])[F:12])[C@@H:14]([NH:15][C:21](=[O:22])[O:23][C:24]([CH3:26])([CH3:27])[CH3:25])[CH2:18][OH:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 66625271HCID 66625271, compound

Product 1

HCID 49800573(2S,3S)-2-(tert-Butoxycarbonylamino)-3-(benzyloxy)-4,4,4-trifluoro-1-butanolYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (S)-tert-butyl 4-((R)-1-(benzyloxy)-2,2,2-trifluoroethyl)-2,2-dimethyloxazolidine-3-carboxylate (1.21 g, 3.1 mmol) in methanol (100 mL) was added p-toluenesulfonic acid monohydrate (90 mg, 0.47 mmol). The mixture was stirred at room temperature for 5 days, then the methanol was removed and the residue was dissolved with EtOAc. The EtOAc solution was washed with saturated aq. Na2CO3 solution, water, brine and dried over Na2SO4. Removal of the solvent gave a residue which was purified by flash chromatography to afford the title compound tert-butyl (2S,3S)-3-(benzyloxy)-4,4,4-trifluoro-1-hydroxybutan-2-ylcarbamate (0.54 g, 90%) and recovered starting material (0.54 g). 1H NMR (400 MHz, CDCl3, □ in ppm) 7.31˜7.39 (m, 5H), 5.21 (d, J=7.6 Hz, 1H), 4.87 (d, J=11.1 Hz, 1H), 4.58 (d, J=11.1 Hz, 1H), 4.13 (m, 1H), 4.00 (d, J=11.7 Hz, 1H), 3.83 (m, 1H), 3.65 (d, J=11.7 Hz, 1H), 1.40 (s, 9H).

Workup

  1. customthe methanol was removed
  2. dissolutionthe residue was dissolved with EtOAc
  3. washThe EtOAc solution was washed with saturated aq. Na2CO3 solution, water, brine
  4. dry with materialdried over Na2SO4
  5. customRemoval of the solvent
  6. customgave a residue which
  7. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-9ec453a8c80c4e049660afba26f99205
Source dataset
uspto-grants-2014_02
Patent number
US08642632B2

Reaction notes

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