ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Phosphorus oxychloride → 7-[2-(2-Formamidothiazol-4-yl)-2-(2,2,2-trifluoroethyoxyimino)acetamido]-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid

HRID 255778
ノート
印刷プレビュー

反応式

HRID 255778 の反応式
C[N+](C)=CCl.[Cl-].P(Cl)(Cl)(Cl)=O.[CH:12]([NH:14][C:15]1[S:16][CH:17]=[C:18]([C:20](=[N:24][O:25][CH2:26][C:27]([F:30])([F:29])[F:28])[C:21]([OH:23])=O)[N:19]=1)=[O:13].[NH2:31][CH:32]1[C:49](=[O:50])[N:34]2[C:35]([C:46]([OH:48])=[O:47])=[C:36]([CH2:39][S:40][C:41]3[S:42][CH:43]=[N:44][N:45]=3)[CH2:37][S:38][C@H:33]12.C[Si](CC(N)=O)(C)C>C(OCC)(=O)C.O.CN(C)C=O>[CH:12]([NH:14][C:15]1[S:16][CH:17]=[C:18]([C:20](=[N:24][O:25][CH2:26][C:27]([F:30])([F:29])[F:28])[C:21]([NH:31][CH:32]2[C:49](=[O:50])[N:34]3[C:35]([C:46]([OH:48])=[O:47])=[C:36]([CH2:39][S:40][C:41]4[S:42][CH:43]=[N:44][N:45]=4)[CH2:37][S:38][C@H:33]23)=[O:23])[N:19]=1)=[O:13]
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 5

HCID 24813Phosphorus oxychlorideHCID 77311Chloro-N,N-dimethylformiminium chlorideHCID 357676Acetamide, 2-(trimethylsilyl)-HCID 128891877-Amino-3-(1,3,4-thiadiazol-2-ylthiomethyl)-3cephem-4-carboxylic acidHCID 540184582-(2,2,2-Trifluoroethoxyimino)-2-(2-formylaminothiazol-4-yl)acetic acid

生成物 1

HCID 131715308
7-[2-(2-Formamidothiazol-4-yl)-2-(2,2,2-trifluoroethyoxyimino)acetamido]-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid
収率 78.4%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒3 回

実験手順

Vilsmeier reagent prepared from N,N-dimethyl formamide (0.2 g.) and phosphoryl chloride (0.42 g.) in a conventional manner was added to ethyl acetate (10 ml.), and then 2-(2-formamidothiazol-4-yl)-2-(2,2,2-trifluoroethoxyimino)acetic acid (syn isomer, 0.75 g.) was added to the solution under ice-cooling and stirred at the same temperature for 30 minutes. The solution was added to a solution of 7-amino-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (0.83 g.) and trimethylsilylacetamide (2.62 g.) in ethyl acetate (30 ml.) at -30° C., and stirred at the same temperature for 1.5 hours. After adding ethyl acetate (100 ml.) and water to the resultant solution, the ethyl acetate layer was separated. Water (100 ml.) was added to the ethyl acetate solution adjusted to pH 7.5 with saturated aqueous solution of sodium bicarbonate. The aqueous layer was separated and the ethyl acetate (150 ml.) was added thereto, and adjusted to pH 1.5 with hydrochloric acid. The ethyl acetate layer was separated, washed with saturated aqueous solution of sodium chloride, dried over magnesium sulfate, and concentrated in vacuo. The residue was triturated with diethyl ether to give 7-[2-(2-formamidothiazol-4-yl)-2-(2,2,2-trifluoroethyoxyimino)acetamido]-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer, 1.2 g.).

後処理

  1. temperaturecooling
  2. stirringstirred at the same temperature for 1.5 hours
  3. customthe ethyl acetate layer was separated
  4. additionWater (100 ml.) was added to the ethyl acetate solution
  5. customThe aqueous layer was separated
  6. additionthe ethyl acetate (150 ml.) was added
  7. customThe ethyl acetate layer was separated
  8. washwashed with saturated aqueous solution of sodium chloride
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated in vacuo
  11. customThe residue was triturated with diethyl ether

出典と根拠

ORDレコード
ord-8c9250b0a03140c28b9b53846b580182
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

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート