1,2-Dichloroethane → Methyl 7-phthalimido-3-methylenecepham-4-carboxylate 1-oxide

HRID 972225Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 972225
[CH3:1][C:2](=[CH2:27])[CH:3]([N:8]1[C:11](=[O:12])[CH:10]([N:13]2[C:17](=[O:18])[C:16]3=[CH:19][CH:20]=[CH:21][CH:22]=[C:15]3[C:14]2=[O:23])[CH:9]1[S:24]([OH:26])=O)[C:4]([O:6][CH3:7])=[O:5].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.ClCCCl.C(OCC)(=O)C>[Cl-].[Na+].O>[C:17]1(=[O:18])[N:13]([CH:10]2[C:11](=[O:12])[N:8]3[CH:3]([C:4]([O:6][CH3:7])=[O:5])[C:2](=[CH2:1])[CH2:27][S:24](=[O:26])[C@H:9]23)[C:14](=[O:23])[C:15]2=[CH:22][CH:21]=[CH:20][CH:19]=[C:16]12

Komponenten

6

Edukt 4

HCID 111,2-DichloroethaneHCID 8857Ethyl AcetateHCID 14812Phosphorus oxide (P4O10)HCID 21314440Methyl 3-methyl-2-(2-sulfino-4-oxo-3-phthalimido-1-azetidinyl)-3-butenoate

Produkt 1

HCID 69799987Methyl 7-phthalimido-3-methylenecepham-4-carboxylate 1-oxide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

A solution of 0.10 g. of methyl 3-methyl-2-(2-sulfino-4-oxo-3-phthalimido-1-azetidinyl)-3-butenoate and 0.04 g. of phosphorous pentoxide in 20 ml. of 1,2-dichloroethane was stirred at room temperature for 1 hour. A tlc of the reaction mixture indicated only trace amounts of the methylenecepham sulfoxide. The mixture was then refluxed for 30 minutes, cooled to room temperature, and combined with 25 ml. of ethyl acetate and 50 ml. of brine. The organic layer was separated, washed with aqueous sodium bicarbonate and brine and dried (MgSO4). Evaporation in vacuo to dryness provided 0.04 g. of the title product as a white froth.

Aufarbeitung

  1. temperatureThe mixture was then refluxed for 30 minutes
  2. customThe organic layer was separated
  3. washwashed with aqueous sodium bicarbonate and brine
  4. dry with materialdried (MgSO4)
  5. customEvaporation in vacuo to dryness
  6. customprovided 0.04 g

Quellen und Nachweise

ORD-Eintrag
ord-f78088c1afc74d1cbe3c508151233b4d
Quelldatensatz
uspto-grants-1977_10
Patentnummer
US04052387

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