Potassium Hydroxide → HCID 46846423, compound

HRID 2039665Notes

Reaction equation

HRID 2039665 reaction equation
[F:1][CH:2]([F:32])[O:3][C:4]1[C:9]2[O:10][C:11]3[CH:16]=[CH:15][C:14]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])=[CH:13][C:12]=3[C:8]=2[C:7]([C:22]2[O:23][CH:24]=[C:25]([C:27]([O:29]CC)=[O:28])[N:26]=2)=[CH:6][CH:5]=1.[OH-].[K+]>C(O)C.O1CCCC1.O>[F:32][CH:2]([F:1])[O:3][C:4]1[C:9]2[O:10][C:11]3[CH:16]=[CH:15][C:14]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])=[CH:13][C:12]=3[C:8]=2[C:7]([C:22]2[O:23][CH:24]=[C:25]([C:27]([OH:29])=[O:28])[N:26]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 46846424HCID 46846424, compound

Product 1

HCID 46846423HCID 46846423, compoundYield 98.4%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a slurry of ethyl 2-(4-(difluoromethoxy)-8-(methylsulfonamido)dibenzo[b,d]furan-1-yl)1,3-oxazole-4-carboxylate (0.2 g, 0.429 mmol) in ethanol (5 mL) and tetrahydrofuran (3 mL) was added potassium hydroxide (0.256 g, 4.562 mmol) in water (0.5 mL). Then it was stirred at room temperature for 16 hours. The solvent was removed in vacuum. The residue was diluted with water and acidified with 1N HCl until the solid separates out. The solid was filtered and washed with hexane. Yield—98.4%. 1H-NMR (DMSO-d6) δ: 3.09 (s, 3H), 7.40 (s, 1H), 7.48-7.51 (m, 1H), 7.59-7.63 (m, 2H), 7.87 (d, 1H), 8.06 (d, 1H), 8.97-8.99 (m, 2H), 9.81 (s, 1H); HPLC (purity): 99.1%; Mass calculated for C18K2F2N2O7S-438.4, observed—437.0; Rf—0.2 (Dichloromethane:Methanol (8:2)).

Workup

  1. customThe solvent was removed in vacuum
  2. additionThe residue was diluted with water
  3. filtrationThe solid was filtered
  4. washwashed with hexane

Sources & evidence

ORD record
ord-57197807015547b39051ffc559dce5c8
Source dataset
uspto-grants-2013_11
Patent number
US08580795B2

Reaction notes

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