Water → cis-4-Acetoxymethyl-3-[2-(2-chloroacetamido-4-thiazolyl)-2-methoxyiminoacetamido]-2-oxoazetidine

HRID 2231564ノート

反応式

HRID 2231564 の反応式
[C:1]([O:4][CH2:5][C@H:6]1[NH:9][C:8](=[O:10])[C@H:7]1[NH2:11])(=[O:3])[CH3:2].C(=O)([O-])O.[Na+].[Cl:17][CH2:18][C:19]([NH:21][C:22]1[S:23][CH:24]=[C:25]([C:27](=[N:31][O:32][CH3:33])[C:28](Cl)=[O:29])[N:26]=1)=[O:20].O>O1CCCC1>[C:1]([O:4][CH2:5][C@H:6]1[NH:9][C:8](=[O:10])[C@H:7]1[NH:11][C:28](=[O:29])[C:27]([C:25]1[N:26]=[C:22]([NH:21][C:19](=[O:20])[CH2:18][Cl:17])[S:23][CH:24]=1)=[N:31][O:32][CH3:33])(=[O:3])[CH3:2]

参加物

6

反応物 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 538001502-(2-Chloroacetamido-4-thiazolyl)-2-methoxyiminoacetyl chlorideHCID 70390316cis-4-Acetoxymethyl-3-amino-2-oxoazetidine

生成物 1

HCID 86740461cis-4-Acetoxymethyl-3-[2-(2-chloroacetamido-4-thiazolyl)-2-methoxyiminoacetamido]-2-oxoazetidine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Under ice-cooling and stirring, 12 ml of an aqueous solution containing 632 mg of cis-4-acetoxymethyl-3-amino-2-oxoazetidine and 1.122 g of sodium hydrogen carbonate is added to a suspension of 2.36 of 2-(2-chloroacetamido-4-thiazolyl)-2-methoxyiminoacetyl chloride (syn-isomer) in 20 ml of tetrahydrofuran. The mixture is stirred for 2 hours at room temperature and the solvent is then distilled off in vacuo to leave the residue, which solidifies. Water is added to the solidified residue, followed by filtration. The collected crystals are washed successively with an aqueous sodium hydrogen carbonate solution, water and ether and dried to give cis-4-acetoxymethyl-3-[2-(2-chloroacetamido-4-thiazolyl)-2-methoxyiminoacetamido]-2-oxoazetidine (syn-isomer), m.p. 180°-190° C. (dec.).

後処理

  1. temperatureUnder ice-cooling
  2. stirringThe mixture is stirred for 2 hours at room temperature
  3. distillationthe solvent is then distilled off in vacuo
  4. customto leave the residue, which
  5. filtrationfollowed by filtration
  6. washThe collected crystals are washed successively with an aqueous sodium hydrogen carbonate solution, water and ether
  7. customdried

出典と根拠

ORDレコード
ord-19c0ace6bf31437eb4c7260f3466f237
出典データセット
uspto-grants-1988_11
特許番号
US04782147

反応ノート

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