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Sulfuric Acid → t-Butyl 7beta-amino-3-methyl-3-cephem-4-carboxylate

HRID 257999
Notes
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Reaction equation

HRID 257999 reaction equation
[CH3:1][C:2]1[CH2:11][S:10][C@@H:5]2[C@H:6]([NH2:9])[C:7](=[O:8])[N:4]2[C:3]=1[C:12]([OH:14])=[O:13].S(=O)(=O)(O)O.[CH3:20][C:21](=[CH2:23])[CH3:22]>COCCOC>[NH2:9][C@@H:6]1[C:7](=[O:8])[N:4]2[C:3]([C:12]([O:14][C:21]([CH3:23])([CH3:22])[CH3:20])=[O:13])=[C:2]([CH3:1])[CH2:11][S:10][C@H:5]12
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 334987-Aminodeacetoxycephalosporanic acid

Product 1

HCID 10869362t-Butyl 7beta-amino-3-methyl-3-cephem-4-carboxylateYield 33.1%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 7-ADCA (10.0 g, 0.0467 mol), ethylene glycol dimethyl ether (80 ml), concentrated sulfuric acid (6.0 ml) and isobutylene (36.0 g, 0.6416 mol) in a pressure bottle was stirred at room temperature for 32 hours. Solvent was removed under reduced pressure. The residue was diluted with methylene chloride, washed with water, sodium bicarbonate solution, brine, dried over sodium sulfate and concentrated to give 4.18 g of t-butyl 7β-amino-3-methyl-3-cephem-4-carboxylate.

Workup

  1. customSolvent was removed under reduced pressure
  2. additionThe residue was diluted with methylene chloride
  3. washwashed with water, sodium bicarbonate solution, brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2ca1d6079258480fa6252f58a9f06534
Source dataset
uspto-grants-1993_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05264429

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes