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

HRID 1487548노트

반응식

HRID 1487548 반응식
[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

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 86695500(4S,5R)-tert-butyl 4-(fluoromethyl)-2,2-dimethyl-5-(4-(3-(methylsulfonamido-methyl)isoxazol-5-yl)phenyl)oxazolidine-3-carboxylate

생성물 1

HCID 86695498(1R,2S)-3-fluoro-1-hydroxy-1-(4-(3-(methylsulfonamidomethyl)isoxazol-5-yl)phenyl)propan-2-aminium chloride

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
0 °C

실험 절차

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 (CI) 344 ([M+H]+.

후처리

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

출처 및 근거

ORD 기록
ord-69b19d344e6a47999794da28fd1dd230
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09428528B2

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