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

HRID 1719281노트

반응식

HRID 1719281 반응식
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]

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 57417360Sodium chloride; water용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-fe74a1f0aa514620a2fc2b8a03bf91b1
출처 데이터셋
uspto-grants-1985_09
특허 번호
US04539152

반응 노트

불러오는 중…