Potassium Carbonate → HCID 68277956, compound

HRID 1526887Notes

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=8.0Hz, 2H), 7.90 (d, J=8.0Hz, 2H), 7.72 (d, J=7.6Hz, 2H), 7.52 (d, J=7.6Hz, 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-02370239d53d41cc85cf137d1ce2691d
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09085570B2

Reaction notes

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