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Dimethylformamide → 7-[2-(2-Formamidothiazol-4-yl)-2-cyanomethoxyiminoacetamido]-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid

HRID 255755
ノート
印刷プレビュー

反応式

HRID 255755 の反応式
P(Cl)(Cl)(Cl)=O.CN(C)C=O.[CH:11]([NH:13][C:14]1[S:15][CH:16]=[C:17]([C:19](=[N:23][O:24][CH2:25][C:26](=O)[NH2:27])[C:20]([OH:22])=O)[N:18]=1)=[O:12].[NH2:29][CH:30]1[C:47](=[O:48])[N:32]2[C:33]([C:44]([OH:46])=[O:45])=[C:34]([CH2:37][S:38][C:39]3[S:40][CH:41]=[N:42][N:43]=3)[CH2:35][S:36][C@H:31]12>CC(C)=O.C(N(CC)CC)C.O1CCCC1>[CH:11]([NH:13][C:14]1[S:15][CH:16]=[C:17]([C:19](=[N:23][O:24][CH2:25][C:26]#[N:27])[C:20]([NH:29][CH:30]2[C:47](=[O:48])[N:32]3[C:33]([C:44]([OH:46])=[O:45])=[C:34]([CH2:37][S:38][C:39]4[S:40][CH:41]=[N:42][N:43]=4)[CH2:35][S:36][C@H:31]23)=[O:22])[N:18]=1)=[O:12]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 128891877-Amino-3-(1,3,4-thiadiazol-2-ylthiomethyl)-3cephem-4-carboxylic acidHCID 538052302-(2-Formamidothiazol-4-yl)-2-carbamoylmethoxyiminoacetic acid

生成物 1

HCID 1317152817-[2-(2-Formamidothiazol-4-yl)-2-cyanomethoxyiminoacetamido]-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid
収率 34.8%

試薬・触媒・溶媒 3

HCID 180Acetone溶媒HCID 8028Tetrahydrofuran溶媒HCID 8471Triethylamine溶媒

実験手順

Phosphoryl chloride (0.96 g.), N,N-dimethylformamide (0.459 g.), tetrahydrofuran (12 ml.) and 2-(2-formamidothiazol-4-yl)-2-carbamoylmethoxyiminoacetic acid (syn isomer, 1.2 g.) were treated in a similar manner to that of Example 1-(1) to give an activated acid solution. After a suspension of 7-amino-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (1.75 g.) in 50% aqueous acetone (16 ml.) was adjusted to pH 7 to 8.5 with triethylamine, the activated acid solution was added to the stirred solution at -5° to 0° C. while keeping at pH 6.5 to 7.5 and stirred at the same temperature for 30 minutes. After removing the solvent from the resultant solution in vacuo, ethyl acetate was added to the residue. The solution was adjusted to pH 1.5 with 10% hydrochloric acid and the insoluble substance was filtered off. The filtrate was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated in vacuo. The residue was pulverized with diethyl ether to give 7-[2-(2-formamidothiazol-4-yl)-2-cyanomethoxyiminoacetamido]-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer, 0.87 g.).

後処理

  1. customto give an activated acid solution
  2. additionthe activated acid solution was added to the stirred solution at -5° to 0° C.
  3. customAfter removing the solvent from the resultant solution in vacuo, ethyl acetate
  4. additionwas added to the residue
  5. filtrationthe insoluble substance was filtered off
  6. extractionThe filtrate was extracted with ethyl acetate
  7. washThe extract was washed with a saturated aqueous solution of sodium chloride
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-cbc6549da07743cea36d49f9ada22982
出典データセット
uspto-grants-1987_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04698337

反応ノート

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