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

HRID 851369ノート

反応式

HRID 851369 の反応式
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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-cc8f39e8662c4a46b7305dad898a92e6
出典データセット
uspto-grants-1983_05
特許番号
US04383945

反応ノート

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