Sulfur trioxide-pyridine → 5-(Tert-butoxycarbonylaminomethyl)furan-2-sulfonic acid

HRID 2067714ノート

反応式

HRID 2067714 の反応式
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[O:11][CH:12]=[CH:13][CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CN=CC=1.[O:21]=[S:22](=[O:24])=[O:23]>ClCCl>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[O:11][C:12]([S:22]([OH:24])(=[O:23])=[O:21])=[CH:13][CH:14]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

4

反応物 2

HCID 168533Sulfur trioxide-pyridineHCID 4935496Tert-butyl (furan-2-ylmethyl)carbamate

生成物 1

HCID 866438015-(Tert-butoxycarbonylaminomethyl)furan-2-sulfonic acid収率 40%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

A solution of 2-(tert-butoxycarbonylaminomethyl)-furan (9.8 g, 50 mmol) in 150 mL of dichloromethane was added into a flask, and the reaction mixture was cooled to 0° C. in an ice bath. A solution of pyridine-sulfur trioxide adduct (15.9 g, 100 mmol) in 100 mL of dichloromethane were added dropwise. Upon completion of the addition, the reaction mixture was allowed to warm to room temperature. The mixture was stirred at room temperature for additional 8 h. After the completion of the reaction, the reaction mixture was then extracted with water (400 mL×2). Aqueous hydrochloric acid (10%) was slowly added dropwise to the aqueous layer. The aqueous layer was adjusted to pH 6.5-7, and extracted with dichloromethane (500 mL×2). The organic layer was washed by saturated brine, and concentrated under reduced pressure to give 5.5 g (40.0% yield) of 5-(tert-butoxycarbonylaminomethyl)furan-2-sulfonic acid.

後処理

  1. additionUpon completion of the addition
  2. temperatureto warm to room temperature
  3. customAfter the completion of the reaction
  4. extractionthe reaction mixture was then extracted with water (400 mL×2)
  5. additionAqueous hydrochloric acid (10%) was slowly added dropwise to the aqueous layer
  6. extractionextracted with dichloromethane (500 mL×2)
  7. washThe organic layer was washed by saturated brine
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-4035de0dd4124628b8b5ab462f12af87
出典データセット
uspto-grants-2012_10
特許番号
US08293895B2

反応ノート

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