Water → 3-(4-Tert-butylbenzyl)-[1,2,3]oxathiazolidine 2,2-dioxide

HRID 2244345Notes

Reaction equation

[C:1]([C:5]1[CH:17]=[CH:16][C:8]([CH2:9][N:10]2[CH2:14][CH2:13][O:12][S:11]2=[O:15])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH2:18]>C(Cl)Cl.C(#N)C>[C:1]([C:5]1[CH:17]=[CH:16][C:8]([CH2:9][N:10]2[CH2:14][CH2:13][O:12][S:11]2(=[O:18])=[O:15])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2-(4-tert-butylbenzylamino)-ethanol (1190 mg, 5.74 mmol) and triethylamine (3200 μl, 22.96 mmol) in DCM (15 ml) at −15° C. was added a solution of thionylchloride (544 μl, 7.46 mmol) in DCM (4 ml) over 10 min. The reaction mixture was stirred at −10° C. for 30 min, filtered and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography to give the desired compound (790 mg, 54%) as a white solid. To a mixture of 3-(4-tert-butylbenzyl)-[1,2,3]oxathiazolidine 2-oxide (790 mg, 3.12 mmol) in DCM (20 ml), acetonitrile (8 ml) and water (8 ml), at 0° C. was added NaIO4 (867 mg, 4.05 mmol) followed by RuO2 (2 mg). The reaction mixture was stirred at 0° C. for 2 h. Water was added and the phases were separated and the aqueous phase was extracted with ethyl acetate. The organic layers were combined washed with brine, dried (MgSO4), and concentrated in vacuo. The residue was then purified by flash column chromatography to give the desired product (640 mg, 76%) as an off white solid. MS (ISP) 287.0 (M+NH4)+.

Workup

customthe phases were separated
extractionthe aqueous phase was extracted with ethyl acetate
washThe organic layers were combined washed with brine
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo
customThe residue was then purified by flash column chromatography

Sources & evidence

ORD record: ord-ef851de67f1f4da1abb24555857e356b
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07678818B2

Reaction notes

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