Hydrochloric Acid → HCID 88737066, compound

HRID 1649406Notes

Reaction equation

HRID 1649406 reaction equation
C[C:2]1(C)[S:6][C@@H:5]2[C@H:7]([NH2:10])[C:8](=[O:9])[N:4]2[C@H:3]1[C:11]([OH:13])=[O:12].Cl[P:16]([NH:19][C:20]1[S:21][CH:22]=[C:23]([C:25](=[CH:29][C:30]2[C:35]([Cl:36])=[CH:34][CH:33]=[CH:32][C:31]=2Cl)[C:26](Cl)=[O:27])[N:24]=1)(Cl)=[O:17].[ClH:38].[OH-:39].[Na+].[O:41]1CCCC1>C(N(CC)CC)C>[OH:39][P:16]([NH:19][C:20]1[S:21][CH:22]=[C:23](/[C:25](=[CH:29]/[C:30]2[C:31]([Cl:38])=[CH:32][CH:33]=[CH:34][C:35]=2[Cl:36])/[C:26]([NH:10][CH:7]2[C:8](=[O:9])[N:4]3[CH:3]([C:11]([OH:13])=[O:12])[CH2:2][S:6][C@H:5]23)=[O:27])[N:24]=1)([OH:17])=[O:41]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2×HCID 110826-Aminopenicillanic acidHCID 14798Sodium HydroxideHCID 53893016HCID 53893016, compound

Product 1

HCID 88737066HCID 88737066, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent3×

Procedure

3 g of 6-aminopenicillanic acid were dissolved in 100 ml of 80 percent strength aqueous tetrahydrofuran with one equivalent of triethylamine. The solution was cooled to 0° and 5 g of the product from Example 40 were introduced, during which the pH of the solution was kept at 7.5 by addition of triethylamine. The mixture was subsequently stirred for 30 minutes and the tetrahydrofuran was then stripped off and the aqueous solution was adjusted to pH 1.8 with 2 N hydrochloric acid. The solution was stirred at this pH for one hour and was then adjusted to pH 6.5 with 2 N sodium hydroxide solution and extracted three times with ethyl acetate. The aqueous phase was adjusted to pH 1.8 again and the product was filtered off, washed with water and dried. It contained one mole of triethylamine. Yield: 7.5 g.

Workup

  1. temperatureThe solution was cooled to 0°
  2. stirringThe solution was stirred at this pH for one hour
  3. extractionextracted three times with ethyl acetate
  4. filtrationthe product was filtered off
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-26db65fbe5b0432eb41be33f4d293292
Source dataset
uspto-grants-1983_11
Patent number
US04416880

Reaction notes

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