Water → HCID 67501587, compound

HRID 1187765Notes

Reaction equation

C(OC([N:8]1[C@@H:12]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]3[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][N:23]=3)=[CH:17][CH:16]=2)[CH2:11][O:10]C1(C)C)=O)(C)(C)C.O.FC(F)(F)C(O)=O>C(#N)C.C(OCC)(=O)C>[NH2:8][C@@H:12]([CH2:13][CH2:14][C:15]1[CH:16]=[CH:17][C:18]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:29])[F:30])=[CH:24][N:23]=2)=[CH:19][CH:20]=1)[CH2:11][OH:10]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of (S)-2,2-dimethyl-4-{2-[4-(5-trifluoromethyl-pyridin-2-ylamino)-phenyl]-ethyl}-oxazolidine-3-carboxylic acid tert-butyl ester (54 mg) in acetonitrile (0.5 ml) were added water (1.5 ml) and trifluoroacetic acid (0.071 ml). The mixture was heated at 80° C. for 2 h. The mixture was then cooled to room temperature and diluted with ethyl acetate. The resulting mixture was washed sequentially with 1 N aq. sodium hydroxide solution and saturated brine, the phases were then separated and the organic phase was dried over sodium sulphate and concentrated in vacuo to afford (S)-2-amino-4-[4-(5-trifluoromethyl-pyridin-2-ylamino)-phenyl]-butan-1-ol (38 mg, quant.) as a yellow oil which was used in the next step without further purification. MS (ISP): 326.3 ([M+H]+).

Workup

temperatureThe mixture was then cooled to room temperature
washThe resulting mixture was washed sequentially with 1 N aq. sodium hydroxide solution and saturated brine
customthe phases were then separated
dry with materialthe organic phase was dried over sodium sulphate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-f1d0f845f53444f88e8e1a0d0f2d8224
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673950B2

Reaction notes

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