Trifluoroacetic acid → HCID 59173172, compound

HRID 885187Notes

Reaction equation

HRID 885187 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[C@@H:19]([CH2:20][C@@H:21]([O:23][C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)[CH3:22])[CH2:18][O:17]C1(C)C)=O)(C)(C)C>O.C(#N)C.C(OCC)(=O)C>[NH2:15][C@@H:19]([CH2:20][C@@H:21]([O:23][C:24]1[CH:25]=[CH:26][C:27]([Cl:30])=[CH:28][CH:29]=1)[CH3:22])[CH2:18][OH:17]

Participants

6

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59173139HCID 59173139, compound

Product 1

HCID 59173172HCID 59173172, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of trifluoroacetic acid (0.85 ml) in water (18 ml) was added dropwise a solution of (S)-4-[(S)-2-(4-chloro-phenoxy)-propyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (1.34 g) in acetonitrile (3 ml). The mixture was heated for 4 h at 80° C. with mechanical shaking. The mixture was then cooled to room temperature and diluted with ethyl acetate. The mixture was washed with aq. sodium bicarbonate solution and then the organic phase was separated, dried over sodium sulphate and concentrated in vacuo to give (2S,4S)-2-amino-4-(4-chloro-phenoxy)-pentan-1-ol (0.76 g, 92%) as an off-white solid. MS (ISP): 232.1 ([{37Cl}M+H]), 230.2 ([{35Cl}M+H]+).

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. washThe mixture was washed with aq. sodium bicarbonate solution
  3. customthe organic phase was separated
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-323476bfd6744a6483b5483e67d98946
Source dataset
uspto-grants-2012_08
Patent number
US08242153B2

Reaction notes

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