Potassium Carbonate → HCID 57663179, compound
Reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:11][C@@H:12]([CH3:16])[CH2:13][O:14][CH3:15])[CH:10]=1)[C:5]([OH:7])=[O:6].F[C:18]1[CH:19]=[CH:20][C:21]2[S:27](=[O:29])(=[O:28])[N:26]([CH3:30])[CH2:25][CH2:24][O:23][C:22]=2[CH:31]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:30][N:26]1[CH2:25][CH2:24][O:23][C:22]2[CH:31]=[C:18]([O:1][C:2]3[CH:3]=[C:4]([CH:8]=[C:9]([O:11][C@@H:12]([CH3:16])[CH2:13][O:14][CH3:15])[CH:10]=3)[C:5]([OH:7])=[O:6])[CH:19]=[CH:20][C:21]=2[S:27]1(=[O:29])=[O:28]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 120 °C
Procedure
A mixture of 3-hydroxy-5-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}benzoic acid (0.2 g, 0.88 mmol), 7-fluoro-2-methyl-3,4-dihydro-2H-5,1,2-benzoxathiazepine 1,1-dioxide (205 mg, 0.88 mmol) and potassium carbonate (244 mg, 1.77 mmol) in acetonitrile (5 mL) was stirred in a microwave reactor at 120° C. for 28 hours. The solvent was removed in vacuo and water (50 mL) and ethyl acetate (50 mL) added. The ethyl acetate layer was separated and discarded and the aqueous layer acidified and extracted into ethyl acetate (2×50 mL). The combined organics were washed with brine, dried (MgSO4), filtered and the solvent removed in vacuo to give the desired compound as a brown oil (0.22 g) which was used in the following steps without further purification. m/z 436 (M−H)−
Workup
- customThe solvent was removed in vacuo and water (50 mL) and ethyl acetate (50 mL)
- additionadded
- customThe ethyl acetate layer was separated
- extractionextracted into ethyl acetate (2×50 mL)
- washThe combined organics were washed with brine
- dry with materialdried (MgSO4)
- filtrationfiltered
- customthe solvent removed in vacuo
Sources & evidence
- ORD record
- ord-b58a653b70e543918e062ee57ae81ed5
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07943607B2
Reaction notes
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