Ethyl Acetate → HCID 178511758, compound

HRID 249596Notes

Reaction equation

HRID 249596 reaction equation
Cl.[C:2]1([CH:8]([O:15][C:16]([C:18]2[N:23]3[C:24](=[O:27])[C@@H:25]([NH2:26])[C@H:22]3[S:21][CH2:20][C:19]=2[CH2:28][S:29][C:30]2[N:31]=[N:32][NH:33][CH:34]=2)=[S:17])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>ClCCl>[C:2]1([CH:8]([O:15][C:16]([C:18]2[N:23]3[C:24](=[O:27])[C@@H:25]([NH2:26])[C@H:22]3[S:21][CH2:20][C:19]=2[CH2:28][S:29][C:30]2[N:31]=[N:32][NH:33][CH:34]=2)=[S:17])[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 178479291HCID 178479291, compound

Product 1

HCID 178511758HCID 178511758, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 7β-phenylacetamido-3-(1,2,3-triazol-4-yl)thiomethylthio-3-cephem-4-carboxylic acid diphenylmethyl ester (629 mg: 1 mMol.) in dichloromethane (7 ml) under ice cooling are added pyridine (162μl : 2 mMol.) and phosphrus pentachloride (380 mg: 1.8 mMol.), and the mixture is stirred at room temperature for 40 minutes. The solution is dropwise added into a solution of 1,3-butanediol (0.46 ml) in dichloromethane (2 ml) at -30° C. After stirring under ice cooling for 30 minutes, the reaction mixture is diluted with water and extracted with dichloromethane. The extract is dried over sodium sulfate and concentrated under reduced pressure. The residue gives powder (518 mg) containing 7β-amino-3-(1,2,3-triazol-4-yl)thiomethylthio-3-cephem-4-carboxylic acid diphenylmethyl ester hydrochloride from ethyl acetate--dichloromethane. This powder (100 mg) is suspended in dichloromethane, shaken with 5% aqueous sodium hydrogen carbonate, dried over sodium sulfate, and concentrated under reduced pressure. The residue is purified by silica gel chromatography to give 7β-amino-3-(1,2,3-triazol-4-yl)thiomethylthio-3-cephem-4-carboxylic acid diphenylmethyl ester (10 mg). Yield: 10%.

Workup

  1. dry with materialdried over sodium sulfate
  2. concentrationconcentrated under reduced pressure
  3. customThe residue is purified by silica gel chromatography

Sources & evidence

ORD record
ord-f9122478eaae4296bf623edccbc2c20e
Source dataset
uspto-grants-1993_05
Patent number
US05214037

Reaction notes

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