Potassium Carbonate → HCID 68277956, compound
Reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([S:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)[CH2:3][CH2:2]1.[Li+].Cl[CH2:19][C:20]1[N:21]=[C:22]([C:26]2[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:28][CH:27]=2)[O:23][C:24]=1[CH3:25].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:25][C:24]1[O:23][C:22]([C:26]2[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:28][CH:27]=2)=[N:21][C:20]=1[CH2:19][S:14]([C:11]1[CH:10]=[CH:9][C:8]([CH2:7][N:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)=[CH:13][CH:12]=1)(=[O:16])=[O:15]Participants
Conditions
- Temperature
- 70 °C
Procedure
A mixture of lithium 4-(morpholinomethyl)benzenesulfinate (2.0 g, 8.10 mmol, 1.43 equiv), methyl 4-(4-(chloromethyl)-5-methyloxazol-2-yl)benzoate (1.5 g, 5.66 mmol, 1.00 equiv) and potassium carbonate (780 mg, 5.65 mmol, 1.00 equiv) in N,N-dimethylformamide (60 mL) was stirred overnight at 70° C. The reaction mixture was cooled to room temperature and the product was precipitated by the addition of 150 mL of ice and water. The solid was collected by filtration, washed with 2×20 mL of water and dried in a vacuum oven to afford 1.5 g (57%) of methyl 4-(5-methyl-4-((4-(morpholinomethyl)phenylsulfonyl)methyl)oxazol-2-yl)benzoate as a white solid. LC-MS: (ES, m/z): 512 [M+CH3CN+H]+, 471 [M+H]+. 1HNMR (400 MHz, DMSO-d6, ppm) δ 8.04 (d, J=8.0 Hz, 2H), 7.90 (d, J=8.0 Hz, 2H), 7.72 (d, J=7.6 Hz, 2H), 7.52 (d, J=7.6 Hz, 2H), 4.67 (s, 2H), 3.88 (s, 3H), 3.55 (s, 6H), 3.31-3.29 (d, 4H), 2.32 (s, 4H), 2.15 (s, 3H).
Workup
- temperatureThe reaction mixture was cooled to room temperature
- customthe product was precipitated by the addition of 150 mL of ice and water
- filtrationThe solid was collected by filtration
- washwashed with 2×20 mL of water
- customdried in a vacuum oven
Sources & evidence
- ORD record
- ord-d33c207674aa46e4befff4bad979da50
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09296732B2
Reaction notes
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