Sulfuric Acid → HCID 68126061, compound

HRID 1579953Notes

Reaction equation

HRID 1579953 reaction equation
S(=O)(=O)(O)O.CN(C)C(=[O:10])C.[C:12]1(=[O:45])[N:16]([CH:17]2[C:38](=[O:39])[N:19]3[CH:20]([C:26]([O:28][CH2:29][C:30]4[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=4)=[O:27])[C:21]([CH3:25])([CH3:24])[S:22](=O)[C@H:18]23)[C:15](=[O:40])[C:14]2=[CH:41][CH:42]=[CH:43][CH:44]=[C:13]12>C(OCC)(=O)C>[C:12]1(=[O:45])[N:16]([CH:17]2[C:38](=[O:39])[N:19]3[CH:20]([C:26]([O:28][CH2:29][C:30]4[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=4)=[O:27])[C@:21]([CH3:24])([OH:10])[CH2:25][S:22][C@H:18]23)[C:15](=[O:40])[C:14]2=[CH:41][CH:42]=[CH:43][CH:44]=[C:13]12

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 31374DimethylacetamideHCID 68126759HCID 68126759, compound

Product 1

HCID 68126061HCID 68126061, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4 drops of conc, sulfuric acid in 60 ml. N,N-dimethylacetamide and 80 ml. of benzene was dried azeotropically for 30 minutes. p-Methoxybenzyl 6-phthalimido-2,2-dimethylpenam-3-carboxylate-1-oxide (5.0 g., 10 mmol) was then added. The reaction mixture was refluxed for 30 minutes, cooled and evaporated to near dryness. Ethyl acetate (150 ml.) was added to the product, and the resulting solution was evaporated in vacuo to dryness. A crystalline product formed during evaporation of the solvent. The product was then slurried with 50 ml. of ethyl acetate. Filtration gave 3.1 grams (62 percent) of p-methoxybenzyl 7-phthalimido-3α-methyl-3β-hydroxycepham-4-carboxylate as colorless crystals, mp 216°-217°: nmr (CDCl3) 76 (3, s, 3-CH3), 149 and 205 (2, ABq, J=14 Hz, 2-CH2), 230 (3, s, OCH3), 274 (1, s, 4-H), 300 (1, broad s, OH), 309 (2, s, ester CH2), 324 (1, d, J=4.5 Hz, azetidinone H), 335 (1, d, J=4.5 Hz, azetidinone H), 426 (4, q, p-CH3OC6H4ArH) and 469 Hz (4, m, phthalimido H); ir (mull) 3460 (OH), 1725 (ester C=O), 1739 and 1781 (phthalimido C=O) and 1802 cm-1 (azetidinone C=O, shoulder).

Workup

  1. dry with materialof benzene was dried azeotropically for 30 minutes
  2. temperatureThe reaction mixture was refluxed for 30 minutes
  3. temperaturecooled
  4. customevaporated
  5. additionEthyl acetate (150 ml.) was added to the product
  6. customthe resulting solution was evaporated in vacuo to dryness
  7. customA crystalline product formed during evaporation of the solvent
  8. filtrationFiltration

Sources & evidence

ORD record
ord-388ff08da5874633942adf40e08627df
Source dataset
uspto-grants-1976_01
Patent number
US03932387

Reaction notes

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