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

HRID 1852190ノート

反応式

HRID 1852190 の反応式
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

参加物

4

反応物 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 57816716HCID 57816716、化合物

生成物 1

HCID 70978761Tert-butyl 1-fluoromethylcyclopropylsulfonylcarbamate収率 72.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d05ba2f8c5084439a66aaeed37dd4dc6
出典データセット
uspto-grants-2015_02
特許番号
US08957203B2

反応ノート

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