Hydrochloric Acid → 7-Aminodeacetoxycephalosporanic acid

HRID 27804

반응식

HRID 27804 반응식
[NH2:1][C@@H:2]1[C:20](=[O:21])[N:4]2[C:5]([C:10]([O:12]CC3C=CC=CC=3)=[O:11])=[C:6]([CH3:9])[CH2:7][S:8][C@H:3]12.C1(OC)C=CC=CC=1.Cl>C(Cl)Cl.[N+](C)([O-])=O.[Ti](Cl)(Cl)(Cl)Cl>[NH2:1][C@@H:2]1[C:20](=[O:21])[N:4]2[C:5]([C:10]([OH:12])=[O:11])=[C:6]([CH3:9])[CH2:7][S:8][C@H:3]12

참가 물질

7

반응물 3

HCID 313Hydrochloric AcidHCID 7519AnisoleHCID 70581629Benzyl 7beta-amino-3-methyl-3-cephem-4-carboxylate

생성물 1

HCID 334987-Aminodeacetoxycephalosporanic acid수율 32%

시약·촉매·용매 3

HCID 24193Titanium Tetrachloride촉매HCID 6344Dichloromethane용매HCID 6375Nitromethane용매

실험 절차

To a solution of benzyl 7β-amino-3-methyl-3-cephem-4-carboxylate (1.2 g) and anisole (5.2 ml) in methylene chloride (100 ml) is added a solution of titanium tetrachloride (2.6 g) in nitromethane under ice cooling, and the mixture stirred for 9.5 hours at room temperature. The reaction mixture is adjusted to pH 1 or less with diluted hydrochloric acid (70 ml), washed with ethyl acetate, and neutralized with 6 N-sodium hydroxide. The resulting titanium hydroxide is removed by filtration, and the filtrate concentrated under reduced pressure at a temperature below 50° C. The resulting crystals are collected by filtration to give 7β-amino-3-methyl-3-cephem-4-carboxylic acid (270 mg). Yield: 32%. This product was identical with an authentic specimen in NMR and IR spectra.

후처리

  1. washwashed with ethyl acetate
  2. customThe resulting titanium hydroxide is removed by filtration
  3. concentrationthe filtrate concentrated under reduced pressure at a temperature below 50° C
  4. filtrationThe resulting crystals are collected by filtration

출처 및 근거

ORD 기록
ord-8c3eb0c41b714b4585ddd5fc572bb3a6
출처 데이터셋
uspto-grants-1980_09
특허 번호
US04223132

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