1,8-Diazabicyclo(5.4.0)undec-7-ene → methyl 2-[(3R,4R)-3-allyl-5,5-dimethyl-1-oxo-2,8-diaza-6-oxaspiro[3,4]oct-7-en-2-yl]-3-methylbut-2-enoate

HRID 1719306ノート

反応式

HRID 1719306 の反応式
N12CCCN=C1CCCCC2.[OH:12][C:13]([C@:16]1([N+:32]#[C-:33])[C@@H:19]([CH2:20][CH:21]=[CH2:22])[N:18]([C:23](=[C:28]([CH3:30])[CH3:29])[C:24]([O:26][CH3:27])=[O:25])[C:17]1=[O:31])([CH3:15])[CH3:14]>C(Cl)Cl.CC(C)=O.C(O)(=O)C>[CH2:20]([C@@H:19]1[C@:16]2([N:32]=[CH:33][O:12][C:13]2([CH3:14])[CH3:15])[C:17](=[O:31])[N:18]1[C:23](=[C:28]([CH3:30])[CH3:29])[C:24]([O:26][CH3:27])=[O:25])[CH:21]=[CH2:22]

参加物

6

反応物 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 53962359methyl 2-[(3R,4R)-3-(1-hydroxy-1-methylethyl)-3-isocyano-2-oxo-4-allylazetidin-1-yl]-3-methylbut-2-enoate

生成物 1

HCID 22823197methyl 2-[(3R,4R)-3-allyl-5,5-dimethyl-1-oxo-2,8-diaza-6-oxaspiro[3,4]oct-7-en-2-yl]-3-methylbut-2-enoate収率 111.8%

試薬・触媒・溶媒 3

HCID 176Acetic Acid触媒HCID 180Acetone溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of 1,8-diazabicyclo[5.4.0]undec-7-ene (17 μl) in methylene chloride (0.1 ml) was added to a solution of methyl 2-[(3R,4R)-3-(1-hydroxy-1-methylethyl)-3-isocyano-2-oxo-4-allylazetidin-1-yl]-3-methylbut-2-enoate (17 mg) in methylene chloride (1 ml) and acetone (1 ml) at 0° C., and the mixture was stirred for 20 hours at ambient temperature. Acetic acid (2 drops) was added to the reaction mixture at 0° C., and the mixture was evaporated in vacuo. The residue was dissolved in ethyl acetate (20 ml), and the solution was washed with 10% aqueous phosphoric acid, brine, phosphate buffer (pH 6.9), aqueous sodium bicarbonate and brine, dried over magnesium sulfate and evaporated in vacuo to give methyl 2-[(3R,4R)-3-allyl-5,5-dimethyl-1-oxo-2,8-diaza-6-oxaspiro[3,4]oct-7-en-2-yl]-3-methylbut-2-enoate (19 mg) as crude crystals.

後処理

  1. customthe mixture was evaporated in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate (20 ml)
  3. washthe solution was washed with 10% aqueous phosphoric acid, brine, phosphate buffer (pH 6.9), aqueous sodium bicarbonate and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo

出典と根拠

ORDレコード
ord-9673b6e0c77246418737b0e2a099b470
出典データセット
uspto-grants-1985_09
特許番号
US04539152

反応ノート

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