Potassium Carbonate → Ethyl 2-[(2,2-Dimethyl-1,3-dioxolan-4-yl)methyl]-2H-thieno[3,2-e]-1,2-thiazine-3-carboxylate 1,1-dioxide

HRID 1490051Notes

Reaction equation

[N+](C1C=CC(S(O[CH2:14][CH:15]2[CH2:19][O:18][C:17]([CH3:21])([CH3:20])[O:16]2)(=O)=O)=CC=1)([O-])=O.[CH2:22]([O:24][C:25](=[O:38])[CH2:26][NH:27][S:28]([C:31]1[S:32][CH:33]=[CH:34][C:35]=1[CH:36]=O)(=[O:30])=[O:29])[CH3:23].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.O>[CH3:21][C:17]1([CH3:20])[O:16][CH:15]([CH2:14][N:27]2[C:26]([C:25]([O:24][CH2:22][CH3:23])=[O:38])=[CH:36][C:35]3[CH:34]=[CH:33][S:32][C:31]=3[S:28]2(=[O:30])=[O:29])[CH2:19][O:18]1

Participants

Conditions

Temperature: 55 °C

Procedure

The product from Step A (46.5 g, 0.292 mol) was added in portions to a solution (room temperature) of (N-[[3-formyl-thien-2-yl]sulfonyl]glycine ethyl ester (27 g, 0.97 mol) in dimethylsulfoxide (200 mL) which contained potassium carbonate (40.45 g, 0.292 mol). This mixture was stirred at 55° C. for 12 h, cooled to 0° C, diluted with water, and extracted with ethyl acetate (3×200 mL). The combined extracts were dried (MgSO4) and evaporated to a crude oil which was purified by column chromatography (silica, 30% ethyl acetate in hexane) to give 18 g (50%) of the desired product as an oil.

Workup

temperaturecooled to 0° C
extractionextracted with ethyl acetate (3×200 mL)
dry with materialThe combined extracts were dried (MgSO4)
customevaporated to a crude oil which
customwas purified by column chromatography (silica, 30% ethyl acetate in hexane)

Sources & evidence

ORD record: ord-aa851c63fdc24798b3fb59b053221a23
Source dataset: uspto-grants-1997_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05681834

Reaction notes

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