Dimethylformamide → HCID 178451131、化合物

HRID 895068

反応式

HRID 895068 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.CN(C)C=O.C(N(CC)CC)C.[C:37]([O:41][C:42]([CH:44]([C:48]1[S:49][CH:50]=[CH:51][CH:52]=1)[C:45](N)=[O:46])=[O:43])([CH3:40])([CH3:39])[CH3:38]>C(N)=O.CCOCC>[C:37]([O:41][C:42]([CH:44]([C:48]1[S:49][CH:50]=[CH:51][CH:52]=1)[C:45]([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:46])=[O:43])([CH3:40])([CH3:38])[CH3:39]

参加物

7

反応物 4

HCID 6228Dimethylformamide2 回HCID 8471TriethylamineHCID 21315147alpha-t-ButoxycarbonylthienylacetamideHCID 178508097HCID 178508097、化合物

生成物 1

HCID 178451131HCID 178451131、化合物

試薬・触媒・溶媒 2

HCID 713Formamide触媒HCID 3283Diethyl Ether溶媒

実験手順

7-Amino-3-(1-carboxymethyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid (1.0 g., 2.68 mmol.) was suspended in 10 ml. of dry dimethylformamide and 1.12 ml. of triethylamine was added followed by 85 drops of formamide. A solution of 0.91 g. (2.68 mmol.) of the activated ester of α-t-butoxycarbonylthienylacetamide, prepared as described above, in 2 ml. of dimethylformamide was added and the reaction mixture was stirred at 25° for three hours. An additional 0.45 g. of activated ester was then added and the mixture stirred another five hours. Ether (ca. 300 ml.) was added and the solution was decanted. The remaining oily material was washed with ether, dissolved in water and the aqueous solution was extracted with ethyl acetate. The pH of the ethyl acetate solution was adjusted to 1.5 by addition of dilute hydrochloric acid. Extraction with ethyl acetate and evaporation of the solvent gave 7-(α-t-butoxycarbonylthienylacetamido)-3-(1-carboxymethyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid.

後処理

  1. stirringthe mixture stirred another five hours
  2. customthe solution was decanted
  3. washThe remaining oily material was washed with ether
  4. dissolutiondissolved in water
  5. extractionthe aqueous solution was extracted with ethyl acetate
  6. additionThe pH of the ethyl acetate solution was adjusted to 1.5 by addition of dilute hydrochloric acid
  7. extractionExtraction
  8. customwith ethyl acetate and evaporation of the solvent

出典と根拠

ORDレコード
ord-3c0bb7e1f7bf4e45b896cdd0ceaf9a1b
出典データセット
uspto-grants-1981_08
特許番号
US04286089

関連ノート

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