N,N-Dimethylaniline → HCID 178429631、化合物

HRID 127653

反応式

HRID 127653 の反応式
O(CC([NH:11][C@@H:12]1[C:23](=[O:24])[N:14]2[C:15]([C:20]([OH:22])=[S:21])=[C:16]([CH3:19])[CH2:17][S:18][C@H:13]12)=O)C1C=CC=CC=1.CN(C)C1C=CC=CC=1.C[Si](C)(Cl)Cl.P(Cl)(Cl)(Cl)(Cl)Cl>C(Cl)Cl.O.O1CCOCC1.C(O)CCC>[NH2:11][C@@H:12]1[C:23](=[O:24])[N:14]2[C:15]([C:20]([OH:22])=[S:21])=[C:16]([CH3:19])[CH2:17][S:18][C@H:13]12

参加物

9

反応物 4

HCID 949N,N-Dimethylaniline2 回HCID 6398DichlorodimethylsilaneHCID 24819Phosphorus pentachlorideHCID 178429632HCID 178429632、化合物

生成物 1

HCID 178429631HCID 178429631、化合物

試薬・触媒・溶媒 4

HCID 2631-Butanol溶媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
-20 °C

実験手順

A suspension of 3.80 g (10 mmols) of 7β-phenoxyacetamido-3-methylthio-ceph-3-em-4-carboxylic acid in 38 ml of absolute methylene chloride is stirred with 4.45 ml of dimethylaniline and 1.50 ml of dimethyldichlorosilane for 30 minutes at room temperature. The reaction mixture is cooled to -20° C., 2.60 g of phosphorus pentachloride are added, the mixture is stirred for 30 minutes at -20° C. and is then added dropwise to a mixture, cooled to -20° C., of 15.5 ml of n-butanol and 1.47 ml of dimethylaniline. The temperature is allowed to rise to -10° C. and 15.5 ml of dioxane and 0.53 ml of water are added. When crystallisation starts, the pH value is adjusted to 4.1 with tributylamine and crystallisation is brought to completion by stirring for 2 hours at 0°-5° C. The precipitate is filtered off, washed with 10 ml of dioxane and 5 ml of methylene chloride and dried in a high vacuum. 7β-Amino-3-methylthio-ceph-3-em-4-carboxylic acid of melting point 205° C. (decomposition) is obtained; UV spectrum (0.1 N NaHCO3): λmax =293 (ε=7600); IR spectrum (nujol): characteristic bands at 3.15, 5.55 6.17 and 6.53μ.

後処理

  1. additionis then added dropwise to a mixture
  2. customto rise to -10° C.
  3. customWhen crystallisation
  4. customthe pH value is adjusted to 4.1 with tributylamine and crystallisation
  5. stirringby stirring for 2 hours at 0°-5° C
  6. filtrationThe precipitate is filtered off
  7. washwashed with 10 ml of dioxane and 5 ml of methylene chloride
  8. customdried in a high vacuum

出典と根拠

ORDレコード
ord-fc782fc3eefe4c5ba419988ea529d6ea
出典データセット
uspto-grants-1981_03
特許番号
US04256739

関連ノート

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