Hydrochloric Acid → methyl 2-[(4R)-4-allyl-3-chloro-2-oxoazetidin-1-yl]-3-methylbut-2-enoate

HRID 1719275노트

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HRID 1719275 반응식
N[C@@H:2]1[C@@H:5]([CH2:6][CH:7]=[CH2:8])[N:4]([C:9](=[C:14]([CH3:16])[CH3:15])[C:10]([O:12][CH3:13])=[O:11])[C:3]1=[O:17].C(ON=O)CC(C)C.[ClH:26].C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(OCC)C.C(OCC)(=O)C>[CH2:6]([C@H:5]1[N:4]([C:9](=[C:14]([CH3:16])[CH3:15])[C:10]([O:12][CH3:13])=[O:11])[C:3](=[O:17])[CH:2]1[Cl:26])[CH:7]=[CH2:8]

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 8053Isoamyl NitriteHCID 516892Sodium BicarbonateHCID 14581224methyl [(3R,4R)-3-amino-4-allyl-2-oxoazetidin-1-yl]-3-methylbut-2-enoate

생성물 1

HCID 54283209methyl 2-[(4R)-4-allyl-3-chloro-2-oxoazetidin-1-yl]-3-methylbut-2-enoate수율 60.8%

시약·촉매·용매 3

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

A solution of methyl 2-[(3R,4R)-3-amino-4-allyl-2-oxoazetidin-1-yl]-3-methylbut-2-enoate (1.0 g) in methylene chloride (10 ml) was cooled to -65° C., and isopentylnitrite (1.01 ml) and a solution of hydrogen chloride (524 mg) in ethyl ether (8 ml) were added. The mixture was allowed to warm to 0° C. during a period of 45 minutes and stirred for one hour and half at 0° C. The reaction mixture was poured into a mixture of ethyl acetate (40 ml) and dilute aqueous sodium bicarbonate. The organic layer was separated and washed with brine, dried ove magnesium sulfate and evaporated to leave an oil, which was chromatographed on silica gel (15 g) eluting with a mixture of methylene chloride and acetone (100:2-100:5) to give methyl 2-[(4R)-4-allyl-3-chloro-2-oxoazetidin-1-yl]-3-methylbut-2-enoate (658 mg) as an oil.

후처리

  1. customat 0° C
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried ove magnesium sulfate
  5. customevaporated
  6. customto leave an oil, which
  7. customwas chromatographed on silica gel (15 g)
  8. washeluting with a mixture of methylene chloride and acetone (100:2-100:5)

출처 및 근거

ORD 기록
ord-396a8ba08c334ec69e8a700ad8e7483d
출처 데이터셋
uspto-grants-1985_09
특허 번호
US04539152

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