(Diethylamino)sulfur trifluoride → Tert-butyl 1-fluoromethylcyclopropylsulfonylcarbamate

HRID 1852190노트

반응식

HRID 1852190 반응식
O[CH2:2][C:3]1([S:6]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])(=[O:8])=[O:7])[CH2:5][CH2:4]1.CCN(S(F)(F)[F:23])CC>C(Cl)Cl>[F:23][CH2:2][C:3]1([S:6]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])(=[O:8])=[O:7])[CH2:5][CH2:4]1

참가 물질

4

반응물 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 57816716HCID 57816716, 화합물

생성물 1

HCID 70978761Tert-butyl 1-fluoromethylcyclopropylsulfonylcarbamate수율 72.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of tert-butyl 1-hydroxymethylcyclopropylsulfonylcarbamate (26 g, 103 mmol) in DCM (300 mL) was cooled to −78° C. To this solution was added DAST (41 mL, 310 mmol) and the reaction mass was stirred at the same temperature for 30 min. The reaction mass was quenched with aqueous 1N NaOH solutions. The organic layer was separated and the aqueous layer was acidified to pH ˜2 by using 1.5 N HCl solutions. The aqueous solution was extracted with DCM (50 mL×4). The combined organic layer was dried over anhydrous sodium sulphate and evaporated to get desired compound (19 g, 72%) as gummy mass. 1H NMR (400 MHz, DMSO-d6): δ ppm 11.25 (sb, 1H), 4.75 (s, 1H), 4.63 (s, 1H), 1.44 (s, 9H), 1.28 (m, 2H), 1.07 (m, 2H). 19F NMR: −211.7 (1F).

후처리

  1. customThe reaction mass was quenched with aqueous 1N NaOH solutions
  2. customThe organic layer was separated
  3. extractionThe aqueous solution was extracted with DCM (50 mL×4)
  4. dry with materialThe combined organic layer was dried over anhydrous sodium sulphate
  5. customevaporated

출처 및 근거

ORD 기록
ord-d05ba2f8c5084439a66aaeed37dd4dc6
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08957203B2

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