Acetic Acid → N-(tert-Butyl)-2-(4-fluorophenyl)-2-oxoethanesulfonamide

HRID 2369963

반응식

HRID 2369963 반응식
[C:1]([NH:5][S:6]([CH3:9])(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.[F:15][C:16]1[CH:25]=[CH:24][C:19]([C:20](OC)=[O:21])=[CH:18][CH:17]=1.C(O)(=O)C>C1COCC1.CCCCCC.C(OCC)(=O)C>[C:1]([NH:5][S:6]([CH2:9][C:20]([C:19]1[CH:24]=[CH:25][C:16]([F:15])=[CH:17][CH:18]=1)=[O:21])(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

8

반응물 4

HCID 176Acetic AcidHCID 67878Methyl 4-fluorobenzoateHCID 4130162N-tert-butylmethanesulfonamideHCID 178418339Butyllithium

생성물 1

HCID 68288463N-(tert-Butyl)-2-(4-fluorophenyl)-2-oxoethanesulfonamide

시약·촉매·용매 3

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매HCID 8857Ethyl Acetate용매

반응 조건

온도
-78 °C

실험 절차

Under inert gas, 1.00 g of N-tert-butylmethanesulfonamide were initially charged in 20 ml of THF and then, at a temperature of −78° C., 9.00 ml of a 1.6 N butyllithium solution in hexane were added dropwise. After stirring with ice cooling for 5 minutes, the mixture was cooled again to −78° C., and a solution, likewise cooled to −78° C., of 1.33 ml of methyl 4-fluorobenzoate in 10 ml of THF was added dropwise. The mixture was allowed to come to room temperature and stirred for 1 hour. The reaction solution was admixed with 0.82 ml of acetic acid, diluted with 50 ml of ethyl acetate, and washed with 40 ml of saturated aqueous sodium hydrogencarbonate solution and 40 ml of saturated aqueous sodium chloride solution. The organic phase was dried over MgSO4 and concentrated by rotary evaporation. The crude product was purified by means of normal phase chromatography using a Flashmaster with an n-heptane/ethyl acetate gradient. The product-containing fractions were combined and concentrated by rotary evaporation. This gave the product (662 mg) with a molecular weight of 273.3 g/mol (C12H16FNO3S).

후처리

  1. additionwas added dropwise
  2. customto come to room temperature
  3. stirringstirred for 1 hour
  4. washwashed with 40 ml of saturated aqueous sodium hydrogencarbonate solution and 40 ml of saturated aqueous sodium chloride solution
  5. dry with materialThe organic phase was dried over MgSO4
  6. concentrationconcentrated by rotary evaporation
  7. customThe crude product was purified by means of normal phase chromatography
  8. concentrationconcentrated by rotary evaporation

출처 및 근거

ORD 기록
ord-3e55d2e9adfd41718b17b6a18e21a01b
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08710050B2

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