Potassium Carbonate → (5,6-Dioxo-2,3,5,6-tetrahydronaphtho[1,2-b][1,4]oxathiin-2-yl)methyl (4-fluorophenyl)carbamate

HRID 563118Notes

Reaction equation

[OH:1][CH2:2][CH:3]1[O:8][C:7]2[C:9]3[C:14]([C:15](=[O:18])[C:16](=[O:17])[C:6]=2[S:5][CH2:4]1)=[CH:13][CH:12]=[CH:11][CH:10]=3.[F:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]=[C:27]=[O:28])=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[F:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:28])[O:1][CH2:2][CH:3]2[O:8][C:7]3[C:9]4[C:14]([C:15](=[O:18])[C:16](=[O:17])[C:6]=3[S:5][CH2:4]2)=[CH:13][CH:12]=[CH:11][CH:10]=4)=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of 2-(hydroxymethyl)-2,3-dihydronaphtho[1,2-b][1,4]oxathiine-5,6-dione (0.13 g, 0.50 mmol) in N,N-dimethylformamide (1.5 mL) was added 1-fluoro-4-isocyanatobenzene (0.024 mL, 0.55 mmol) and potassium carbonate (0.026 g, 0.50 mmol). The mixture was stirred at 40° C. for 3 hours. The reaction mixture was filtered and the filtrate concentrated under reduced pressure. The crude mixture was purified by flash column chromatography (SiO2, 10% methanol in EtOAc) to give the product as a purple solid (0.051 g, 26%). M.p.=235-237° C.; 300 MHz 1H NMR (DMSO-d6) δ: 9.89 (s, 1H), 7.89 (d, J=7.5, 1H), 7.71 (br. s, 2H), 7.50 (m, 3H), 7.12 (m, 2H), 4.78 (m, 1H), 4.53 (m, 2H), 3.18 (m, 2H); LCMS: 400 [M+H].

Workup

filtrationThe reaction mixture was filtered
concentrationthe filtrate concentrated under reduced pressure
customThe crude mixture was purified by flash column chromatography (SiO2, 10% methanol in EtOAc)

Sources & evidence

ORD record: ord-93a00b41171647f29531be54903c9f23
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08067459B2

Reaction notes

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