Hydrochloric Acid → Ampicillin Trihydrate

HRID 862873Notes

Reaction equation

HRID 862873 reaction equation
[CH3:1][C:2]1([CH3:24])[S:6][C@@H:5]2[C@H:7]([NH:10][C:11]([C@H:13]([NH2:20])[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[O:12])[C:8](=[O:9])[N:4]2[C@H:3]1[C:21]([OH:23])=[O:22].Cl>>[CH3:1][C:2]1([CH3:24])[S:6][C@@H:5]2[C@H:7]([NH:10][C:11]([C@H:13]([NH2:20])[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:12])[C:8](=[O:9])[N:4]2[C@H:3]1[C:21]([OH:23])=[O:22].[OH2:9].[OH2:9].[OH2:9]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 6249Ampicillin

Product 1

HCID 23565Ampicillin Trihydrate

Procedure

The resultant crude protected ampicillin mixture is worked up by treating with a mixture of 289 ml ice-water and 39.6 ml concentrated HCl and stirred for 30 minutes while cooling with ice. The aqueous phase is separated off and the organic phase back-extracted with a mixture of 5.4 ml concentrated HCl and 44.5 ml water. The combined aqueous phases are filtered through a filtering aid and pumped into a suspension of 5 g ampicillin trihydrate seed crystals in 100 ml water keeping the pH from 4.5 to 5.0 by the addition of concentrated aqueous ammonia. The title compound is obtained by standing the mixture overnight in a refrigerator, isolating the crystals, and washing them with 60 ml ice-water and 3×50 ml 90% acetone, followed by drying. Yield 61.6 g=82.4%, Purity 98.8%.

Workup

  1. temperaturewhile cooling with ice
  2. customThe aqueous phase is separated off
  3. extractionthe organic phase back-extracted with a mixture of 5.4 ml concentrated HCl and 44.5 ml water
  4. filtrationThe combined aqueous phases are filtered through a filtering aid
  5. additionpumped into a suspension of 5 g ampicillin trihydrate seed crystals in 100 ml water keeping the pH from 4.5 to 5.0
  6. additionby the addition of concentrated aqueous ammonia

Sources & evidence

ORD record
ord-20c839c4b3da4afbb6b8ddfdadd95be6
Source dataset
uspto-grants-1998_02
Patent number
US05719276

Reaction notes

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