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

HRID 972225ノート

反応式

HRID 972225 の反応式
[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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 57417360Sodium chloride; water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f78088c1afc74d1cbe3c508151233b4d
出典データセット
uspto-grants-1977_10
特許番号
US04052387

反応ノート

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