Sodium Bicarbonate → Methyl cis-3-[2-(2-chloroacetamido-4-thiazolyl)-2-allyloxyiminoacetamido]-2-oxoazetidine-4-carboxylate

HRID 621057ノート

反応式

HRID 621057 の反応式
[NH2:1][C@H:2]1[C@@H:5]([C:6]([O:8][CH3:9])=[O:7])[NH:4][C:3]1=[O:10].C(=O)([O-])O.[Na+].Cl.[Cl:17][CH2:18][C:19]([NH:21][C:22]1[S:23][CH:24]=[C:25](/[C:27](=[N:31]/[O:32][CH2:33][CH:34]=[CH2:35])/[C:28](Cl)=[O:29])[N:26]=1)=[O:20]>O1CCCC1.O>[Cl:17][CH2:18][C:19]([NH:21][C:22]1[S:23][CH:24]=[C:25]([C:27](=[N:31][O:32][CH2:33][CH:34]=[CH2:35])[C:28]([NH:1][C@H:2]2[C@@H:5]([C:6]([O:8][CH3:9])=[O:7])[NH:4][C:3]2=[O:10])=[O:29])[N:26]=1)=[O:20]

参加物

6

反応物 3

HCID 516892Sodium BicarbonateHCID 21244940(2Z)-2-[2-[(2-chloroacetyl)amino]-1,3-thiazol-4-yl]-2-prop-2-enoxyiminoacetyl chloride;hydrochlorideHCID 53988551cis-3-Amino-4-methoxycarbonyl-2-oxoazetidine

生成物 1

HCID 86740476Methyl cis-3-[2-(2-chloroacetamido-4-thiazolyl)-2-allyloxyiminoacetamido]-2-oxoazetidine-4-carboxylate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

In a mixture of 2 ml of tetrahydrofuran and 2 ml of water is dissolved 185.5 mg of methyl cis-3-amino-2-oxoazetidine-4-carboxylate and under ice-cooling and stirring 469.6 mg of sodium hydrogen carbonate and successively, 600 mg of 2-(2-chloroacetamido-4-thiazolyl)-(Z)-allyloxyiminoacetyl chloride hydrochloride is added. The mixture is stirred at room temperature for 2 hours and concentrated under reduced pressure. To the residue is added 20 ml of water and the insolubles are collected by filtration, washed with aqueous sodium hydrogen carbonate, water, hexane and ether in this order, and dried to give methyl cis-3-[2-(2-chloroacetamido-4-thiazolyl)-2-allyloxyiminoacetamido]-2-oxoazetidine-4-carboxylate (syn isomer) as light-yellow granules, m.p. 270°-280° C. (decomp.).

後処理

  1. temperatureunder ice-cooling
  2. concentrationconcentrated under reduced pressure
  3. additionTo the residue is added 20 ml of water
  4. filtrationthe insolubles are collected by filtration
  5. washwashed with aqueous sodium hydrogen carbonate, water, hexane and ether in this order
  6. customdried

出典と根拠

ORDレコード
ord-b634d9f732a54c48b9c668b31dcccdd4
出典データセット
uspto-grants-1989_04
特許番号
US04822790

反応ノート

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