Acetic Acid → 3-(2,2-dioxido-1,4-dihydro-3H-2,1,3-benzothiadiazin-3-yl)propan-1-ol

HRID 2237465Notes

Reaction equation

[Si]([O:18][CH2:19][CH2:20][CH2:21][N:22]1[CH2:27][C:26]2[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=2[NH:24][S:23]1(=[O:33])=[O:32])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(O)(=O)C>O1CCCC1.O>[O:33]=[S:23]1(=[O:32])[N:22]([CH2:21][CH2:20][CH2:19][OH:18])[CH2:27][C:26]2[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=2[NH:24]1

Participants

Conditions

Temperature: 23 °C

Procedure

A solution of 3-(3-{[tert-butyl(diphenyl)silyl]oxy}propyl)-3,4-dihydro-1H-2,1,3-benzothiadiazine 2,2-dioxide (0.44 g, 0.92 mmol) in tetrahydrofuran (4 mL) was treated with tetrabutylammonium fluoride (1.4 mL of a 1 M solution in tetrahydrofuran, 1.4 mmol) and acetic acid (0.16 mL, 2.8 mmol), and stirred at 23° C. for 18 hours. The reaction mixture was diluted with H2O (50 mL) and extracted with dichloromethane (2×50 mL), dried (Na2SO4), and evaporated. Flash chromatography (SiO2, 2.5-100% ethyl acetate/hexanes) provided 3-(2,2-dioxido-1,4-dihydro-3H-2,1,3-benzothiadiazin-3-yl)propan-1-ol (0.20 g, 90%) as a colorless oil:

Workup

extractionextracted with dichloromethane (2×50 mL)
dry with materialdried (Na2SO4)
customevaporated

Sources & evidence

ORD record: ord-e2714c51cd8c4aca94ee1c1038f43de5
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07718652B2

Reaction notes

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