Hydrochloric Acid → HCID 70590633, compound

HRID 904061Notes

Reaction equation

HRID 904061 reaction equation
C(=O)([O-])[O-:2].[Na+].[Na+].[NH2:7][CH:8]1[C:19](=[O:20])[N:10]2[CH:11]([C:16]([OH:18])=[O:17])[C:12]([CH3:15])([CH3:14])[S:13][C@H:9]12.[C:21](Cl)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.OOS([O-])=O.[K+].Cl>O.CC(C)=O>[C:21]([NH:7][CH:8]1[C:19](=[O:20])[N:10]2[CH:11]([C:16]([OH:18])=[O:17])[C:12]([CH3:15])([CH3:14])[S:13](=[O:2])[C@H:9]12)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 10340Sodium CarbonateHCID 12228589HCID 12228589, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 70590633HCID 70590633, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Conditions

Temperature
2 °C

Procedure

To 150 ml. of water were added 11.6 grams (110 millimoles) of sodium carbonate followed by 100 ml. of acetone. To the mixture then were added portion-wise 10.8 grams (50 millimoles) of 6-amino-2,2-dimethylpenam-3-carboxylic acid. The resulting suspension was stirred for about one hour with formation of an almost clear solution. The mixture then was cooled to 2° C., pH 10.2. Benzoyl chloride (6.4 ml.; 55 millimoles) was added dropwise over a 9 minute period (pH 7.4) followed by dropwise addition over a 5 minute period of 16.9 grams of Oxone® in 80 ml. of water. A 6° C. exotherm was noticed. The resulting suspension was stirred in an ice bath for 1 hour. The pH of the resulting mixture was 7.0. Concentrated hydrochloric acid (9 ml.) was added to pH 2.0, and the mixture was extracted twice with ethyl acetate. The organic layer was dried over sodium sulfate and evaporated to dryness. A small amount of ethyl acetate was added to the residue, and the product was allowed to crystallize overnight at room temperature to afford 11.6 grams (69%) of 6-benzamido-2,2-dimethylpenam-3-carboxylic acid 1-oxide.

Workup

  1. customA 6° C. exotherm
  2. stirringThe resulting suspension was stirred in an ice bath for 1 hour
  3. extractionthe mixture was extracted twice with ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customevaporated to dryness
  6. additionA small amount of ethyl acetate was added to the residue
  7. customto crystallize overnight at room temperature

Sources & evidence

ORD record
ord-5f1fd4dc310b4e73a3236b530950db69
Source dataset
uspto-grants-1980_10
Patent number
US04230620

Reaction notes

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