Trifluoroacetic acid → 1-(9b-morpholino-3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,9b-dihydro-3aH-chromeno[3,4-d]isoxazol-7-yl)ethane-1,2-diol

HRID 1506427노트

반응식

HRID 1506427 반응식
CC1(C)[O:6][CH:5]([C:7]2[CH:8]=[CH:9][C:10]3[C:19]4([N:20]5[CH2:25][CH2:24][O:23][CH2:22][CH2:21]5)[CH:15]([C:16]([C:26]5[O:30][N:29]=[C:28]([C:31]6[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=6)[C:27]=5[C:37]([F:40])([F:39])[F:38])=[N:17][O:18]4)[CH2:14][O:13][C:11]=3[CH:12]=2)[CH2:4][O:3]1.C(O)(C(F)(F)F)=O>>[O:23]1[CH2:24][CH2:25][N:20]([C:19]23[C:10]4[CH:9]=[CH:8][C:7]([CH:5]([OH:6])[CH2:4][OH:3])=[CH:12][C:11]=4[O:13][CH2:14][CH:15]2[C:16]([C:26]2[O:30][N:29]=[C:28]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[C:27]=2[C:37]([F:40])([F:38])[F:39])=[N:17][O:18]3)[CH2:21][CH2:22]1

참가 물질

3

반응물 2

HCID 6422Trifluoroacetic acidHCID 671717007-(2,2-dimethyl-1,3-dioxolan-4-yl)-9b-morpholino-3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,9b-dihydro-3aH-chromeno[3,4-d]isoxazole

생성물 1

HCID 671683261-(9b-morpholino-3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,9b-dihydro-3aH-chromeno[3,4-d]isoxazol-7-yl)ethane-1,2-diol

실험 절차

A mixture of 7-(2,2-dimethyl-1,3-dioxolan-4-yl)-9b-morpholino-3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,9b-dihydro-3aH-chromeno[3,4-d]isoxazole (Preparation 60D, 0.080 g, 0.140 mmol) and TFA (3.00 ml, 38.9 mmol) was stirred at room temperature for 60 min. The TFA was removed under reduced pressure, and the residue was diluted with dichloromethane, washed with a saturated aqueous solution of sodium bicarbonate, and dried over anhydrous sodium sulfate. Concentration under reduced pressure afforded a quantitative yield of 1-(9b-morpholino-3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,9b-dihydro-3aH-chromeno[3,4-d]isoxazol-7-yl)ethane-1,2-diol as a yellow oil. The product had an HPLC ret. time=2.63 min.−Column: Chromolith SpeedROD 4.6×50 mm (4 min.); Solvent A=10% MeOH, 90% H2O, 0.1% TFA; Solvent B=90% MeOH, 10% H2O, 0.1% TFA. LC/MS M+1=532.0.

후처리

  1. customThe TFA was removed under reduced pressure
  2. additionthe residue was diluted with dichloromethane
  3. washwashed with a saturated aqueous solution of sodium bicarbonate
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationConcentration under reduced pressure

출처 및 근거

ORD 기록
ord-1981987f07a74f1bbf3c7be634538a3c
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216972B2

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