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Sodium Carbonate → 7-[2-(2-Formamidothiazol-4-yl)-2-(3-isoxazolylmethoxyimino)acetamido]-3-cephem-4-carboxylic acid

HRID 1758422
ノート
印刷プレビュー

反応式

HRID 1758422 の反応式
P(Cl)(Cl)(Cl)=O.[CH:6]([NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14](=[N:18][O:19][CH2:20][C:21]2[CH:25]=[CH:24][O:23][N:22]=2)[C:15]([OH:17])=O)[N:13]=1)=[O:7].[NH2:26][CH:27]1[C:37](=[O:38])[N:29]2[C:30]([C:34]([OH:36])=[O:35])=[CH:31][CH2:32][S:33][C@H:28]12.C(=O)([O-])[O-].[Na+].[Na+]>O.CC(C)=O.O1CCCC1.CN(C)C=O>[CH:6]([NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14](=[N:18][O:19][CH2:20][C:21]2[CH:25]=[CH:24][O:23][N:22]=2)[C:15]([NH:26][CH:27]2[C:37](=[O:38])[N:29]3[C:30]([C:34]([OH:36])=[O:35])=[CH:31][CH2:32][S:33][C@H:28]23)=[O:17])[N:13]=1)=[O:7]
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 12941984(6R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidHCID 537376352-(2-Formamidothiazol-4-yl)-2-[(3-isoxazolyl)methoxyimino]acetic acid

生成物 1

HCID 1317123347-[2-(2-Formamidothiazol-4-yl)-2-(3-isoxazolylmethoxyimino)acetamido]-3-cephem-4-carboxylic acid収率 77.4%

試薬・触媒・溶媒 4

HCID 180Acetone溶媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Phosphoryl chloride (1.02 g.), 2-(2-formamidothiazol-4-yl)-2-(3-isoxazolylmethoxyimino)acetic acid (syn isomer, 1.0 g.), N,N-dimethylformamide (0.448 g.) and tetrahydrofuran (10 ml.) were treated in a similar manner to that of Example 5-(1) to give an activated acid solution. On the other hand, a mixture of 7-amino-3-cephem-4-carboxylic acid (0.91 g.), tetrahydrofuran (10 ml.) acetone (5 ml.) and water (5 ml.) was adjusted to pH 7.5 with 20% aqueous sodium carbonate at 0° to -5° C. The activated acid solution was added dropwise to the above solution at 0° to -5° C. while keeping at pH 7.5 to 8.0. The mixture was treated in a similar manner to that of Example 5-(1) to give 7-[2-(2-formamidothiazol-4-yl)-2-(3-isoxazolylmethoxyimino)acetamido]-3-cephem-4-carboxylic acid (syn isomer, 1.25 g.).

後処理

  1. customto give an activated acid solution
  2. additionThe activated acid solution was added dropwise to the above solution at 0° to -5° C.
  3. additionThe mixture was treated in a similar manner to that of Example 5-(1)

出典と根拠

ORDレコード
ord-5f2f9ca4c26f4ec18193f34c864a825e
出典データセット
uspto-grants-1983_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04372952

反応ノート

読み込み中…

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