Methyl chloroacetate → 2-Benzo[1,3]dioxol-5-ylmethyl-4-hydroxy-1,1-dioxo-1,2-dihydro-1lambda6-benzo[e][1,2]thiazine-3-carboxylic acid methyl ester

HRID 1449538Notes

Reaction equation

[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][N:11]3[C:15](=[O:16])[C:14]4[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=4[S:12]3(=[O:22])=[O:21])=[CH:9][C:4]=2[O:3][CH2:2]1.Cl[CH2:24][C:25]([O:27][CH3:28])=[O:26].[H-].[Na+]>CS(C)=O.Cl>[CH3:28][O:27][C:25]([C:24]1[N:11]([CH2:10][C:8]2[CH:7]=[CH:6][C:5]3[O:1][CH2:2][O:3][C:4]=3[CH:9]=2)[S:12](=[O:22])(=[O:21])[C:13]2[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=2[C:15]=1[OH:16])=[O:26]

Participants

Conditions

Temperature: 40 °C

Procedure

To 2-Benzo[1,3]dioxol-5-ylmethyl-1,1-dioxo-1,2-dihydro-1λ6 -benzo[d]isothiazol-3-one (1.115 g, 3.517 mmol) in DMSO(6 mL) was added methyl 2-chloroacetate (0.61 mL, 6.96 mmol). The mixture was heated to 40° C. and sodium hydride (0.562 g, 60% in oil, 14 mmol) was added slowly over 1 hour. The mixture was maintained at 40° C. for 3 h and then cooled to room temperature and diluted with 1N HCl (100 mL). The mixture was extracted with ethylacetate (2×100 mL) and the organic phase washed with brine and dried over MgSO4. Chromatography, silica gel, eluant CHCl3, and crystallization from methylene chloride/hexane afforded the required product (0.596 g, 44%);

Workup

temperatureThe mixture was maintained at 40° C. for 3 h
temperaturecooled to room temperature
extractionThe mixture was extracted with ethylacetate (2×100 mL)
washthe organic phase washed with brine
dry with materialdried over MgSO4
customChromatography, silica gel, eluant CHCl3, and crystallization from methylene chloride/hexane

Sources & evidence

ORD record: ord-53f862b6414e420a9ce34a265621d867
Source dataset: uspto-grants-1997_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05599811

Reaction notes

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