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

HRID 851369노트

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HRID 851369 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 over 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 over 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-cc8f39e8662c4a46b7305dad898a92e6
출처 데이터셋
uspto-grants-1983_05
특허 번호
US04383945

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