4-Toluenesulfonyl chloride → tert-butyl N-{2-[(4-methylbenzenesulfonyl)oxy]ethyl}carbamate

HRID 1351125ノート

反応式

HRID 1351125 の反応式
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[OH:12][CH2:13][CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19].C(N(CC)CC)C.[Cl-].C[NH+](C)C.CCCC(C)C>ClCCl.C(OCC)(=O)C>[S:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)([O:12][CH2:13][CH2:14][NH:15][C:16]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:22])(=[O:9])=[O:8]

参加物

8

反応物 5

HCID 73974-Toluenesulfonyl chlorideHCID 78922-MethylpentaneHCID 8471TriethylamineHCID 11649Trimethylazanium;chlorideHCID 2733206tert-butyl N-(2-hydroxyethyl)carbamate

生成物 1

HCID 10781634tert-butyl N-{2-[(4-methylbenzenesulfonyl)oxy]ethyl}carbamate収率 66.1%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

A solution of p-toluenesulfonyl chloride (28.40 g, 148 mmol) in dichloromethane (100 mL) was added dropwise over 30 minutes at 0° C. to a mixture of tert-butyl N-(2-hydroxyethyl)carbamate (20 g, 120 mmol), triethylamine (18.80 g, 186 mmol) and trimethylammonium chloride (1.18 g, 12.4 mmol) in dichloromethane (120 mL). The mixture was stirred at 0° C. for 1 hour then filtered, washing with dichloromethane (100 mL). The filtrate was washed with 10% citric acid (3×100 mL) and brine (100 mL). The organic layer was dried with magnesium sulfate and then filtered. The filtrate was concentrated under reduced pressure to give an oil. The oil was dissolved in ethyl acetate (40 mL) and then iso-hexane (160 mL) was added slowly. The resultant slurry was stirred at room temperature for 17 hours and then filtered. The collected solid was washed with iso-hexane (240 mL) to yield the sub-title compound as a colourless powder (25 g, 64%).

後処理

  1. filtrationthen filtered
  2. washwashing with dichloromethane (100 mL)
  3. washThe filtrate was washed with 10% citric acid (3×100 mL) and brine (100 mL)
  4. dry with materialThe organic layer was dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customto give an oil
  8. stirringThe resultant slurry was stirred at room temperature for 17 hours
  9. filtrationfiltered
  10. washThe collected solid was washed with iso-hexane (240 mL)

出典と根拠

ORDレコード
ord-d2a81df856c94dea964e72b07e3794d3
出典データセット
uspto-grants-2007_05
特許番号
US07217708B2

反応ノート

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