Water → HCID 178514550、化合物

HRID 1111789

反応式

HRID 1111789 の反応式
[NH2:1][CH:2]1[C:23](=[O:24])[N:4]2[C:5]([C:20]([OH:22])=[O:21])=[C:6]([CH:9]([S:14][C:15]3[NH:19][N:18]=[N:17][N:16]=3)[CH2:10][C:11]([OH:13])=[O:12])[CH2:7][S:8][C@H:3]12.O.CN1CCOCC1.[N:33]([CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[CH2:43][C:44](Cl)=[O:45])=[N+:34]=[N-:35]>CC(C)=O>[N:33]([CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[CH2:43][C:44]([NH:1][CH:2]1[C:23](=[O:24])[N:4]2[C:5]([C:20]([OH:22])=[O:21])=[C:6]([CH:9]([S:14][C:15]3[NH:16][N:17]=[N:18][N:19]=3)[CH2:10][C:11]([OH:13])=[O:12])[CH2:7][S:8][C@H:3]12)=[O:45])=[N+:34]=[N-:35]

参加物

6

反応物 4

HCID 962WaterHCID 79724-MethylmorpholineHCID 227677832-Azidomethylphenylacetyl ChlorideHCID 178508097HCID 178508097、化合物

生成物 1

HCID 178514550HCID 178514550、化合物

試薬・触媒・溶媒 1

HCID 180Acetone溶媒2 回

反応条件

温度
0 °C

実験手順

7-Amino-3-(1-carboxymethyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid (3 g., 0.008 mole) was suspended in 50 ml. of water. The suspension was cooled to 0° C. and then N-methylmorpholine (3 g., 0.03 mole) was added. After a solution was obtained, 50 ml. of acetone was added. An acetone solution of 2-azidomethylphenylacetyl chloride (prepared from 2 g. of 2-azidomethylphenyl acetic acid and 2 ml. of thionyl chloride in 100 ml. of methylene chloride) was added dropwise at 0° to 5° C. over 10 minutes. The resulting mixture was stirred for one hour and then the acetone was distilled off with the aid of vacuum. The aqueous layer was extracted once with 50 ml. of toluene. To the aqueous layer was added 50 ml. of ethyl acetate and the pH was adjusted to 2.6 using phosphoric acid (85% diluted with equal volume of water). The ethyl acetate layer was carbon treated and dried over anhydrous sodium sulfate. After filtration the solution was concentrated to give 7-(2-azidomethylphenylacetamido)-3-(1-carboxymethyltetrazol-5-ylthiomethyl)-3-cephem-4-caboxylic acid as a foam-like product which weighed 3.6 g. NMR and IR spectroscopy data were consistent with the expected structure. A small sample was hydrogenated in water using Raney nickel as catalyst to give a product which was identical in every way to an authentic sample of 7-(2-aminomethylphenylacetamido)-3-(1-carboxymethyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid (III).

後処理

  1. customAfter a solution was obtained
  2. distillationthe acetone was distilled off with the aid of vacuum
  3. extractionThe aqueous layer was extracted once with 50 ml
  4. additionTo the aqueous layer was added 50 ml
  5. additiontreated
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationAfter filtration the solution
  8. concentrationwas concentrated

出典と根拠

ORDレコード
ord-1e76250c4ad64ab5ab0f5f4d1e404869
出典データセット
uspto-grants-1978_10
特許番号
US04118563

関連ノート

読み込み中…