Hydrochloric Acid → 7-[2-Amino(phenyl)acetamido]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 975185Notes

Reaction equation

HRID 975185 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:14](=[O:15])[N:13]3[C:16]([C:21]([OH:23])=[O:22])=[C:17]([Cl:20])[CH2:18][S:19][C@H:12]23)=[O:9])=[CH:5][CH:6]=1.Cl>>[NH2:24][CH:7]([C:4]1[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1)[C:8]([NH:10][CH:11]1[C:14](=[O:15])[N:13]2[CH:12]1[S:19][CH2:18][C:17]([Cl:20])=[C:16]2[C:21]([OH:23])=[O:22])=[O:9]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 51039Cefaclor

Product 1

HCID 26097-[2-Amino(phenyl)acetamido]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Conditions

Temperature
15 °C

Procedure

The resultant crude protected Cefaclor mixture is worked up by treating with a mixture of 13.5 ml ice-water and 2.0 ml concentrated HCl and stirred for 25 minutes while cooling with ice. The aqueous phase is separated off and the organic phase is back-extracted with 1.25 ml ice-water. The combined aqueous phases are mixed with 30 ml dimethylformamide, and the resulting suspension is cooled to 15° C., filtered and the solid washed with 8 ml dimethylformamide, which are added to the filtrate. The final solution is treated slowly with concentrated aqueous ammonia to bring the pH to 6.8. The cristalline suspension is stirred at 20° C. for 1 hour, filtered and the crystals washed with 16 ml acetone. After drying, 5.86 g of the title compound were obtained as dimethylformamide solvate.

Workup

  1. temperaturewhile cooling with ice
  2. customThe aqueous phase is separated off
  3. extractionthe organic phase is back-extracted with 1.25 ml ice-water
  4. additionThe combined aqueous phases are mixed with 30 ml dimethylformamide
  5. filtrationfiltered
  6. washthe solid washed with 8 ml dimethylformamide, which
  7. additionare added to the filtrate
  8. additionThe final solution is treated slowly with concentrated aqueous ammonia
  9. stirringThe cristalline suspension is stirred at 20° C. for 1 hour
  10. filtrationfiltered
  11. washthe crystals washed with 16 ml acetone
  12. customAfter drying

Sources & evidence

ORD record
ord-c15d0380a00a49f7b069e7f3861d19dc
Source dataset
uspto-grants-1997_03
Patent number
US05608055

Reaction notes

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