Pyridine → Methyl (S)-4,4-difluoro-2-isocyanato-5-phenylpentanoate

HRID 1913327ノート

反応式

HRID 1913327 の反応式
[NH2:1][C@@H:2]([CH2:7][C:8]([F:17])([F:16])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:3]([O:5][CH3:6])=[O:4].N1C=CC=CC=1.[C:24](Cl)(Cl)=[O:25].C1(C)C=CC=CC=1>ClCCl>[F:17][C:8]([F:16])([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:7][C@H:2]([N:1]=[C:24]=[O:25])[C:3]([O:5][CH3:6])=[O:4]

参加物

6

反応物 4

HCID 1049PyridineHCID 1140TolueneHCID 6371PhosgeneHCID 59430997Methyl (S)-2-amino-4,4-difluoro-5-phenylpentanoate

生成物 1

HCID 86635603Methyl (S)-4,4-difluoro-2-isocyanato-5-phenylpentanoate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

Under argon, methyl (S)-2-amino-4,4-difluoro-5-phenylpentanoate (400 mg, 1.64 mmol) was dissolved in 20 ml of dichloromethane. At RT, pyridine (520 mg, 4 eq.) was added dropwise and the resulting solution was stirred for 15 minutes. The mixture was then cooled to 0° C. and admixed with 20% phosgene solution in toluene (2.16 ml, 4.1 mmol, 2.5 eq.). The mixture was stirred at RT for 90 minutes and then the solvent was removed under reduced pressure. The mixture was codistilled with 10 ml of toluene twice more. The crude product thus obtained was used for the reactions which followed without further purification.

後処理

  1. stirringThe mixture was stirred at RT for 90 minutes
  2. customthe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-d376d74409874d739343bb7fa87e5651
出典データセット
uspto-grants-2013_12
特許番号
US08609681B2

反応ノート

読み込み中…