Benzyl chloroformate → 4-(4-Benzyloxycarbonylamino-2-fluorophenoxy)pyridine-2-carboxylic acid methyl ester

HRID 492837ノート

反応式

HRID 492837 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[C:9]([O:11][C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][C:13]=2[F:19])[CH:8]=[CH:7][N:6]=1)=[O:4].C(=O)([O-])O.[Na+].Cl[C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27]>CC(C)=O.O>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[C:9]([O:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:26]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:27])=[CH:14][C:13]=2[F:19])[CH:8]=[CH:7][N:6]=1)=[O:4]

参加物

6

反応物 3

HCID 10387Benzyl chloroformate2 回HCID 516892Sodium BicarbonateHCID 574708564-(4-Amino-2-fluorophenoxy)pyridine-2-carboxylic acid methyl ester

生成物 1

HCID 576777514-(4-Benzyloxycarbonylamino-2-fluorophenoxy)pyridine-2-carboxylic acid methyl ester収率 70.6%

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 962Water溶媒

実験手順

4-(4-Amino-2-fluorophenoxy)pyridine-2-carboxylic acid methyl ester (11.5 g) was dissolved in acetone (340 ml) and water (170 ml). Next, sodium hydrogencarbonate (17.3 g) was added to the reaction mixture, benzyl chloroformate (9.79 ml) was added while cooling in an ice water bath, and the mixture was stirred for 15 minutes. The reaction mixture was allowed to warm to room temperature and then the mixture was stirred for 2 hours. Benzyl chloroformate (2.45 ml) was further added to the reaction mixture while cooling in an ice water bath, and the mixture was stirred for 18 hours. After concentrating the reaction mixture under reduced pressure, ethyl acetate (500 ml) and brine (200 ml) were added to the resultant residue for partition. The separated organic layer was washed with water (100 ml) and brine (200 ml) and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and then ethyl acetate (50 ml) and hexane (30 ml) were added to the resultant solid for suspension. After filtering the solid, it was subjected to aeration drying to provide the title compound (9.6 g, 70.6%) as a pale yellow solid.

後処理

  1. additionwas added
  2. temperaturewhile cooling in an ice water bath
  3. stirringthe mixture was stirred for 2 hours
  4. temperaturewhile cooling in an ice water bath
  5. stirringthe mixture was stirred for 18 hours
  6. concentrationAfter concentrating the reaction mixture under reduced pressure, ethyl acetate (500 ml) and brine (200 ml)
  7. additionwere added to the resultant residue
  8. customfor partition
  9. washThe separated organic layer was washed with water (100 ml) and brine (200 ml)
  10. dry with materialdried over anhydrous sodium sulfate
  11. distillationThe solvent was distilled off under reduced pressure
  12. additionethyl acetate (50 ml) and hexane (30 ml) were added to the resultant solid for suspension
  13. filtrationAfter filtering the solid, it
  14. customdrying

出典と根拠

ORDレコード
ord-76ac164ab2b840a983d6c797dc6402d8
出典データセット
uspto-grants-2009_05
特許番号
US07531532B2

反応ノート

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