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 1506427Notes

Reaction equation

HRID 1506427 reaction equation
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

Participants

3

Reactant 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

Product 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

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-1981987f07a74f1bbf3c7be634538a3c
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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