Trifluoroacetic acid → HCID 59173172, compound

HRID 1807922Notes

Reaction equation

HRID 1807922 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 phse was separated, dried over sodium sulphate and concentrated in vacuo to give (25,45)-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. temperaturewas then cooled to room temperature
  2. washThe mixture was washed with aq. sodium bicarbonate solution
  3. customthe organic phse was separated
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e2f195c3f2154953ad5db0515aad12a7
Source dataset
uspto-grants-2013_01
Patent number
US08357712B2

Reaction notes

Loading…