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

HRID 1481643노트

반응식

HRID 1481643 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.C(N(S(F)(F)[F:23])CC)C>C(Cl)Cl>[C:12]([O:11][C:10](=[O:16])[NH:9][S:6]([C:3]1([CH2:2][F:23])[CH2:5][CH2:4]1)(=[O:8])=[O:7])([CH3:15])([CH3:14])[CH3:13]

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 (26.0 g, 103 mmol) in DCM (300 mL) was cooled to −78° C. To this solution was added diethylaminosulfur trifluoride (“DAST”, 41.0 mL, 310 mmol). The reaction mass was stirred at the same temperature for 30 min. The reaction mass was quenched with aqueous 1N NaOH solution. The organic layer was discarded and the aqueous layer was acidified to pH˜2 by using aq. 1.5 N HCl solution. The aqueous solution was extracted with DCM (50 mL×4). The combined organic layers were dried over anhydrous sodium sulfate; filtered; then concentrated to afford desired tert-butyl(1-(fluoromethyl)cyclopropyl)sulfonylcarbamate (19 g, 72%) as gummy solid. 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 solution
  2. extractionThe aqueous solution was extracted with DCM (50 mL×4)
  3. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthen concentrated

출처 및 근거

ORD 기록
ord-0ad406a537c34faf87a03ec0ae61f668
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09409943B2

반응 노트

불러오는 중…