Triethylamine → HCID 131711626, compound

HRID 28016Notes

Reaction equation

HRID 28016 reaction equation
[S:1]([N:11]1[C:15](=[O:16])[C:14]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]2[C:12]1=[O:21])([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].C(N(CC)CC)C.[Na+:29].[S:30]1[CH:34]=[CH:33][CH:32]=[C:31]1[CH2:35][C:36]([NH:38][C@@H:39]1[C:51](=[O:52])[N:41]2[C:42]([C:48]([O-:50])=[O:49])=[C:43]([CH2:46][OH:47])[CH2:44][S:45][C@H:40]12)=[O:37]>CN(C)C=O.O>[Na+:29].[S:30]1[CH:34]=[CH:33][CH:32]=[C:31]1[CH2:35][C:36]([NH:38][C@@H:39]1[C:51](=[O:52])[N:41]2[C:42]([C:48]([O-:50])=[O:49])=[C:43]([CH2:46][O:47][C:15](=[O:16])[C:14]3[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=3[C:12](=[O:21])[NH:11][S:1]([C:4]3[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=3)(=[O:3])=[O:2])[CH2:44][S:45][C@H:40]12)=[O:37]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2141332-((4-Methylphenyl)sulfonyl)-1H-isoindole-1,3(2H)-dioneHCID 23695995Desacetylcephalothin sodium

Product 1

HCID 131711626HCID 131711626, compoundYield 58.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In N,N-dimethylformamide (40 ml) is dissolved in 7β-(2-thienylacetamido)-3-hydroxymethyl-3-cephem-4-carboxylic acid sodium salt (3.8 g), followed by the addition of N-tosylphthalimide (4.0 g) and triethylamine (2.0 ml) in that order. The mixture is stirred at room temperature for 4 hours. The reaction mixture is poured in water (100 ml) and rinsed with ethyl acetate. The aqueous layer is adjusted to pH 2.0 with dilute phosphoric acid and extracted with ethyl acetate. The extract is dried and, then, a solution of sodium 2-ethylhexanoate in isopropyl alcohol is added. By this procedure is obtained 7β-(2-thienylacetamido)-3-[2-(N-tosylcarbamoyl) benzoyloxy]methyl-3-cephem-4-carboxylic acid sodium salt (4.0 g).

Workup

  1. washrinsed with ethyl acetate
  2. extractionextracted with ethyl acetate
  3. customThe extract is dried
  4. additiona solution of sodium 2-ethylhexanoate in isopropyl alcohol is added

Sources & evidence

ORD record
ord-5bf41c9eee674cbeb5ae848a5e81ec75
Source dataset
uspto-grants-1980_09
Patent number
US04224441

Reaction notes

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