Hydrochloric Acid → HCID 178525027, compound

HRID 1707456Notes

Reaction equation

HRID 1707456 reaction equation
[C:1]1([CH:7]([O:14][C:15]([C:17]2[N:22]3[C:23](=[O:26])[C@@H:24]([NH2:25])[C@H:21]3[S:20][CH2:19][C:18]=2[S:27][CH2:28][S:29][C:30]2[N:31]=[N:32][NH:33][CH:34]=2)=[O:16])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:35][CH:36]([CH2:38][C:39](O)=[S:40])[F:37].CN1CCOCC1.P(Cl)(Cl)(OC1C=CC=CC=1)=O.Cl>ClCCl.O>[C:1]1([CH:7]([O:14][C:15]([C:17]2[N:22]3[C:23](=[O:26])[C@@H:24]([NH:25][C:39](=[S:40])[CH2:38][CH:36]([F:37])[F:35])[C@H:21]3[S:20][CH2:19][C:18]=2[S:27][CH2:28][S:29][C:30]2[N:31]=[N:32][NH:33][CH:34]=2)=[O:16])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 13038Phosphorodichloridic acid, phenyl esterHCID 178511754HCID 178511754, compoundHCID 178526193HCID 178526193, compound

Product 1

HCID 178525027HCID 178525027, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-30 °C

Procedure

To a solution of 7β-amino-3-(1,2,3-triazol-4-ylthiomethylthio)-3-cephem-4-carboxylic acid diphenylmethyl ester (550 mg: 1.08 mMol.) and difluoromethylthioacetic acid (160 mg: 1.13 mMol.) in dichloromethane (8 ml) cooling at -30° C. are added N-methylmorpholine (0.27 ml: 2.46 mMol.) and phenyl dichlorophosphate (0.19 ml: 1.27 mMol.), and the mixture is stirred at -30° C. for 1 hour. The reaction mixture is mixed with 10% hydrochloric acid (1 ml), diluted with water, and extracted with ethyl acetate. The extract is washed with aqueous saline, dried over sodium sulfate, and concentrated. The residue is purified by silica get column chromatography (toluene: ethyl acetate=1:1) to give 7β-difluoromethylthioacetamido-3-(1,2,3-triazol-4-ylthiomethyl- thio)-3-cephem-4-carboxylic acid diphenylmethyl ester (475 mg) as pale yellow foam. Yield: 69%.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract is washed with aqueous saline
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue is purified by silica
  6. customget column chromatography (toluene: ethyl acetate=1:1)

Sources & evidence

ORD record
ord-249c9013d1074d909cefa2c81fadcede
Source dataset
uspto-grants-1994_10
Patent number
US05352792

Reaction notes

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