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Pivaloyl chloride → 7-[2-(6-formamidopyridin-2-yl)acetamido]-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid

HRID 2286630
ノート
印刷プレビュー

反応式

HRID 2286630 の反応式
C(Cl)(=O)C(C)(C)C.[CH:8]([NH:10][C:11]1[N:16]=[C:15]([CH2:17][C:18]([OH:20])=O)[CH:14]=[CH:13][CH:12]=1)=[O:9].[NH2:21][CH:22]1[C:40](=[O:41])[N:24]2[C:25]([C:37]([OH:39])=[O:38])=[C:26]([CH2:29][S:30][C:31]3[N:35]([CH3:36])[N:34]=[N:33][N:32]=3)[CH2:27][S:28][C@H:23]12>C(Cl)Cl>[CH:8]([NH:10][C:11]1[N:16]=[C:15]([CH2:17][C:18]([NH:21][CH:22]2[C:40](=[O:41])[N:24]3[C:25]([C:37]([OH:39])=[O:38])=[C:26]([CH2:29][S:30][C:31]4[N:35]([CH3:36])[N:34]=[N:33][N:32]=4)[CH2:27][S:28][C@H:23]23)=[O:20])[CH:14]=[CH:13][CH:12]=1)=[O:9]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 62493Pivaloyl chlorideHCID 130208137-Amino-3-(1-methyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylicacidHCID 130601732-(6-Formamidopyridin-2-yl)acetic acid

生成物 1

HCID 886754457-[2-(6-formamidopyridin-2-yl)acetamido]-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid収率 50.5%

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒
3 回

実験手順

A solution of pivaloyl chloride (1.07 g.) in methylene chloride (3 ml.) was added to a solution of 2-(6-Formamidopyridin-2-yl)acetic acid (1.6 g.) and 1,5-diazabicyclo[5,4,0]undecene-5(1.35 g.) in methylene chloride (25 ml.) at -20° to -25° C., and stirred at the same temperature for one hour [solution A]. On the other hand, a solution of 7-amino-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (3.24 g.) and 1,5-diazabicyclo[5,4,0]undecene-5 (1.35 g.) in methylene chloride (60 ml.) was stirred at room temperature for 10 minutes. To the solution was added the above solution A at -20° to -25° C. and stirred at the same temperature for 1.5 hours. After removing the solvent from the resultant solution, ethyl acetate, water and sodium bicarbonate were added to the residue. The aqueous layer was separated and washed with ethyl acetate. Ethyl acetate (300 ml.) was added to the aqueous solution, adjusted to pH 2 to 3 with 5% hydrochloric acid, and then shaken sufficiently. The ethyl acetate layer was separated, washed with water and concentrated under reduced pressure to give 7-[2-(6-formamidopyridin-2-yl)acetamido]-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (2.2 g.).

後処理

  1. customAfter removing the solvent from the resultant solution, ethyl acetate, water and sodium bicarbonate
  2. additionwere added to the residue
  3. customThe aqueous layer was separated
  4. washwashed with ethyl acetate
  5. additionEthyl acetate (300 ml.) was added to the aqueous solution
  6. stirringshaken sufficiently
  7. customThe ethyl acetate layer was separated
  8. washwashed with water
  9. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-0171308b1fac46b69d2c12337709d18b
出典データセット
uspto-grants-1981_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04267176

反応ノート

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