Hydrochloric Acid → (1R,2S)-3-fluoro-1-hydroxy-1-(4-(3-(methylsulfonamidomethyl)isoxazol-5-yl)phenyl)propan-2-aminium chloride

HRID 1520545Notes

Reaction equation

[F:1][CH2:2][C@@H:3]1[C@@H:7]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[O:18][N:17]=[C:16]([CH2:19][NH:20][S:21]([CH3:24])(=[O:23])=[O:22])[CH:15]=3)=[CH:10][CH:9]=2)[O:6]C(C)(C)[N:4]1C(OC(C)(C)C)=O.[ClH:34].O>O1CCOCC1>[Cl-:34].[F:1][CH2:2][C@@H:3]([NH3+:4])[C@H:7]([OH:6])[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:18][N:17]=[C:16]([CH2:19][NH:20][S:21]([CH3:24])(=[O:23])=[O:22])[CH:15]=2)=[CH:10][CH:9]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To (4S,5R)-tert-butyl 4-(fluoromethyl)-2,2-dimethyl-5-(4-(3-(methylsulfonamido-methyl)isoxazol-5-yl)phenyl)oxazolidine-3-carboxylate (300 mg, 0.62 mmol) is added 4N HCl in dioxane (4 ml) at room temperature. The solution is then cooled to 0° C. and water (0.5 ml) is added. The ice bath is removed after ten minutes and the reaction is stirred at room temperature for one hour. The volatiles were then removed by rotary evaporation. Several evaporation cycles were performed using acetonitrile to ensure complete removal of water and excess HCl gave the title compound (234 mg): m/z (Cl) 344 ([M+H]+.

Workup

customThe ice bath is removed after ten minutes
customThe volatiles were then removed by rotary evaporation
customSeveral evaporation cycles
customremoval of water and excess HCl

Sources & evidence

ORD record: ord-aeabfc772e984de0ab3083e18055c31a
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073894B2

Reaction notes

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