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Pyridine → 4-Nitrobenzyl 7-amino-3-mesyloxy-3-cephem-4-carboxylate

HRID 434775
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HRID 434775 반응식
C1(CC([NH:10][CH:11]2[C:36](=[O:37])[N:13]3[C:14]([C:23]([O:25][CH2:26][C:27]4[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=4)=[O:24])=[C:15]([O:18][S:19]([CH3:22])(=[O:21])=[O:20])[CH2:16][S:17][C@H:12]23)=O)C=CC=CC=1.N1C=CC=CC=1.P(Cl)(Cl)(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>C(Cl)Cl.O.CO>[NH2:10][CH:11]1[C:36](=[O:37])[N:13]2[C:14]([C:23]([O:25][CH2:26][C:27]3[CH:28]=[CH:29][C:30]([N+:33]([O-:35])=[O:34])=[CH:31][CH:32]=3)=[O:24])=[C:15]([O:18][S:19]([CH3:22])(=[O:20])=[O:21])[CH2:16][S:17][C@H:12]12
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 1049PyridineHCID 24819Phosphorus pentachlorideHCID 516892Sodium BicarbonateHCID 883895734-Nitrobenzyl 7-(2-phenylacetamido)-3-mesyloxy-3-cephem-4-carboxylate

생성물 1

HCID 887293804-Nitrobenzyl 7-amino-3-mesyloxy-3-cephem-4-carboxylate수율 102%

시약·촉매·용매 3

HCID 887
Methanol
용매
HCID 962Water용매
HCID 6344Dichloromethane용매

실험 절차

To a suspension of 4-nitrobenzyl 7-(2-phenylacetamido)-3-mesyloxy-3-cephem-4-carboxylate (11 g.) in methylene chloride (100 ml.) were added pyridine (2.37 g.) at ambient temperature and then phosphorus pentachloride (5.4 g.) at 0° C. with stirring, whereafter the mixture was stirred at -3° to 3° C. for 2 hours. After adding methanol (5.2 g.) at -20° C., the stirring was continued at the same temperature for additional an hour. The reaction mixture was poured into water and adjusted to pH 7.5 with sodium bicarbonate, followed by extraction with ethyl acetate (500 ml.). The extract was washed with an aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was pulverized with diethyl ether to give 4-nitrobenzyl 7-amino-3-mesyloxy-3-cephem-4-carboxylate (8.8 g.).

후처리

  1. waitthe stirring was continued at the same temperature for additional an hour
  2. extractionfollowed by extraction with ethyl acetate (500 ml.)
  3. washThe extract was washed with an aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-5401077fce9f425ea61bf4905b2613d9
출처 데이터셋
uspto-grants-1983_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04399277

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