Hydrochloric Acid → Ampicillin Trihydrate

HRID 610451

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

Reactant 2

HCID 313Hydrochloric Acid

HCID 6249Ampicillin

Product 1

HCID 23565Ampicillin Trihydrate

Procedure

The mixture obtained in step a) is added dropwise to the mixture obtained in step b) at a temperature of -45/-35°. The resultant mixture is stirred for 2 hours at a temperature of -15/-35°. The resultant crude protected ampicillin mixture is worked up by treating with a mixture of ice-water and concentrated hydrochloric acid and stirred for 20 minutes while cooling with ice. The aqueous phase is separated off and the organic phase is reextracted with a mixture of water and concentrated hydrochloric acid. The combined aqueous phases are treated with concentrated aqueous sodium hydroxide to a pH of 4.5/5.5. Ampicillin trihydrate crystallizes out of the reaction mixture overnight in a refrigerator, the crystals are isolated, washed with IPA 88% and dried. Yield 89.0%, Purity 98.4%.

Workup

temperaturewhile cooling with ice
customThe aqueous phase is separated off
additionthe organic phase is reextracted with a mixture of water and concentrated hydrochloric acid
additionThe combined aqueous phases are treated with concentrated aqueous sodium hydroxide to a pH of 4.5/5.5
customAmpicillin trihydrate crystallizes out of the reaction mixture overnight in a refrigerator
customthe crystals are isolated
washwashed with IPA 88%
customdried

Sources & evidence

ORD record: ord-29d57cd435354d7bbcdd88b43453a9d6
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05998610

Linked notes

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