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

HRID 434775
Notes
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Reaction equation

HRID 434775 reaction equation
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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

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.).

Workup

  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

Sources & evidence

ORD record
ord-5401077fce9f425ea61bf4905b2613d9
Source dataset
uspto-grants-1983_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04399277

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes