Hydrochloric Acid → HCID 86748173, compound

HRID 35996Notes

Reaction equation

HRID 35996 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.O.Cl>CN(C=O)C.C(N(CC)CC)C>[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 962WaterHCID 8434EthylparabenHCID 5284585Loracarbef

Product 1

HCID 86748173HCID 86748173, compoundYield 98.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
45 °C

Procedure

To loracarbef:ethyl paraben (15.0 g, 49.1% potency as loracarbef), predisolved in 150 ml DMF and 15 ml H2O was added concentrated hydrochloric acid (2.53 ml) dropwise. The solution was heated to 45° C. and the pH was raised from 1.84 to 4.0 over 45 minutes using triethylamine. After crystallization began, triethylamine was slowly added until a pH of 6.7 was obtained. The mixture was stirred for 1 hour at 45° C., filtered, washed with DMF and ethanol and dried under vacuum at 40° C. HPLC analysis indicated that no ethyl paraben was present. The actual yield was 10.07 g, 72% as loracarbef activity, the theoretical yield was 7.37 g of loracarbef activity, and the percent yield was 98.4% yield.

Workup

  1. temperaturethe pH was raised from 1.84 to 4.0 over 45 minutes
  2. customAfter crystallization
  3. additiontriethylamine was slowly added until a pH of 6.7
  4. customwas obtained
  5. filtrationfiltered
  6. washwashed with DMF and ethanol
  7. customdried under vacuum at 40° C

Sources & evidence

ORD record
ord-038ea891360c4fcb94b4274519f2fd3a
Source dataset
uspto-grants-1995_05
Patent number
US05412094

Reaction notes

Loading…