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

HRID 72368

反応式

HRID 72368 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
-78 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d9e78386e9b545f2982926e7c48c89da
出典データセット
uspto-grants-2014_09
特許番号
US08828994B2

関連ノート

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