Hydrochloric Acid → Ampicilloic acid

HRID 1982362Notes

Reaction equation

HRID 1982362 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].O.O.O.[OH-].[Na+].Cl.CC([OH:34])C>O>[CH3:1][C:2]1([CH3:24])[S:6][C@H:5]([C@H:7]([NH:10][C:11]([C@H:13]([NH2:20])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:12])[C:8]([OH:9])=[O:34])[NH:4][C@H:3]1[C:21]([OH:23])=[O:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 14798Sodium Hydroxide2×HCID 23565Ampicillin Trihydrate

Product 1

HCID 6914605Ampicilloic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ampicilloic acid was prepared in the following manner. Ampicillin trihydrate (10 gm, Sigma) was suspended in 50 ml of water and dissolved by the addition of 10N NaOH. The pH was maintained at 12 by the addition of 10N NaOH. After 1 hour, the pH was adjusted to 7.0 with 6N HCl. 2-Propanol (140 ml) was then added, and the solution allowed to stand for 4 hours at 4° C., after which time crystals had formed. The crystals were filtered and washed several times with cold 2-propanol:water (3:1) and allowed to dry at room temperature. Thin layer chromatography confirmed that this material was essentially all ampicilloic acid. Yield was 1.97 gm.

Workup

  1. waitto stand for 4 hours at 4° C.
  2. customafter which time crystals had formed
  3. filtrationThe crystals were filtered
  4. washwashed several times with cold 2-propanol:water (3:1)
  5. customto dry at room temperature

Sources & evidence

ORD record
ord-406dccb9ac07470fa1fad60565335882
Source dataset
uspto-grants-1986_06
Patent number
US04596768

Reaction notes

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