2,6-Lutidine → methyl 2-[(3R,4R)-3-isocyano-2-oxo-4-allylazetidin-1-yl]-3-methylbut-2-enoate

HRID 1719281ノート

反応式

HRID 1719281 の反応式
N1C(C)=CC=CC=1C.P(Cl)(Cl)(Cl)=O.[CH:14]([NH:16][C@@H:17]1[C@@H:20]([CH2:21][CH:22]=[CH2:23])[N:19]([C:24](=[C:29]([CH3:31])[CH3:30])[C:25]([O:27][CH3:28])=[O:26])[C:18]1=[O:32])=O.C(OCC)(=O)C>ClCCl.[Cl-].[Na+].O>[N+:16]([C@@H:17]1[C@@H:20]([CH2:21][CH:22]=[CH2:23])[N:19]([C:24](=[C:29]([CH3:31])[CH3:30])[C:25]([O:27][CH3:28])=[O:26])[C:18]1=[O:32])#[C-:14]

参加物

7

反応物 4

HCID 79372,6-LutidineHCID 8857Ethyl AcetateHCID 24813Phosphorus oxychlorideHCID 22823198methyl 2-[(3R,4R)-3-formamido-2-oxo-4-allylazetidin-1-yl]-3-methylbut-2-enoate

生成物 1

HCID 54071546methyl 2-[(3R,4R)-3-isocyano-2-oxo-4-allylazetidin-1-yl]-3-methylbut-2-enoate収率 84.7%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
0 °C

実験手順

2,6-Lutidine (3.82 ml) and phosphorus oxychloride (1.37 ml) were added to a solution of methyl 2-[(3R,4R)-3-formamido-2-oxo-4-allylazetidin-1yl]-3-methylbut-2-enoate (970 mg) in dichloromethane (10 ml) at 0° C., and the mixture was stirred for three hours at 0° C. Then, the reaction mixture was poured into a mixture of ethyl acetate (100 ml) and brine (50 ml). The organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The oily residue was chromategraphed on silica gel (15 g) eluting with a mixture of hexane and ethyl acetate (10:1-3:1) to give methyl 2-[(3R,4R)-3-isocyano-2-oxo-4-allylazetidin-1-yl]-3-methylbut-2-enoate (766 mg) as an oil.

後処理

  1. washThe organic layer was washed with brine
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo
  4. washeluting with a mixture of hexane and ethyl acetate (10:1-3:1)

出典と根拠

ORDレコード
ord-fe74a1f0aa514620a2fc2b8a03bf91b1
出典データセット
uspto-grants-1985_09
特許番号
US04539152

反応ノート

読み込み中…