Hydrochloric Acid → HCID 86748173, compound

HRID 35995Notes

Reaction equation

HRID 35995 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]([C@@H:7]([NH2:24])[C:8]([NH:10][C@@H:11]2[C:18](=[O:19])[N:17]3[C@@H:12]2[CH2:13][CH2:14][C:15]([Cl:23])=[C:16]3[C:20]([OH:22])=[O:21])=[O:9])=[CH:5][CH:6]=1.C(OC(C1C=CC(O)=CC=1)=O)C.Cl.C(N(CC)CC)C>CN(C=O)C.O>[CH:1]1[CH:2]=[CH:3][C:4]([C@@H:7]([NH2:24])[C:8]([NH:10][C@@H:11]2[C:18](=[O:19])[N:17]3[C@@H:12]2[CH2:13][CH2:14][C:15]([Cl:23])=[C:16]3[C:20]([OH:22])=[O:21])=[O:9])=[CH:5][CH:6]=1.[CH3:16][N:17]([CH:18]=[O:19])[CH3:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8434EthylparabenHCID 8471TriethylamineHCID 5284585Loracarbef

Product 1

HCID 86748173HCID 86748173, compoundYield 85.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of loracarbef: ethyl paraben (1.34 g, 65.5% potency as loracarbef) in 18 ml of DMF and 1.8 ml of H2O was added concentrated hydrochloric acid sufficient to obtain a clear solution. The pH of the solution was slowly raised to 6.9 with triethylamine, and the crystallization of the titled product occurred quickly. The mixture was stirred for 1 hour at room temperature, filtered, washed with a solution of 10:1/DMF:H2O, and dried under a vacuum at 40° C. HPLC analysis indicated that no ethyl paraben was present. The actual yield was 1.01 g, 73.9% potency as loracarbef, the theoretical yield was 0.87 g as loracarbef, and the percent yield was 85.3%.

Workup

  1. customto obtain a clear solution
  2. customthe crystallization of the titled product
  3. filtrationfiltered
  4. washwashed with a solution of 10:1/DMF
  5. dry with materialH2O, and dried under a vacuum at 40° C

Sources & evidence

ORD record
ord-302a57457e9144709bb08cffbe0ed74d
Source dataset
uspto-grants-1995_05
Patent number
US05412094

Reaction notes

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