Formic Acid → HCID 53900303, compound

HRID 1632481Notes

Reaction equation

HRID 1632481 reaction equation
C([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:42][O:43][CH3:44])[C:27]([NH:29][CH:30]2[C:37](=[O:38])[N:36]3[CH:31]2[CH2:32][S:33][CH:34]=[C:35]3[C:39]([O-:41])=[O:40])=[O:28])[N:25]=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Na+].C(O)=O>O>[NH2:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:42][O:43][CH3:44])[C:27]([NH:29][CH:30]2[C:37](=[O:38])[N:36]3[CH:31]2[CH2:32][S:33][CH:34]=[C:35]3[C:39]([OH:41])=[O:40])=[O:28])[N:25]=1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 86739680HCID 86739680, compound

Product 1

HCID 53900303HCID 53900303, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

The 297 mg of the product of Step A were suspended in 1.5 ml of aqueous 66% formic acid solution and the mixture was stirred at 50° C. for 15 minutes and was then cooled to room temperature. 0.66 ml of water were added to the mixture which was then filtered and the filter was rinsed with water. A little ethanol was added to the filtrate which was then evaporated to dryness under reduced pressure. The oil residue was taken up in water and ethanol and the mixture was again evaporated to dryness. The residue was added to 2 ml of a 1 M solution of sodium bicarbonate solution and 1.65 ml of water to form a solution which was then filtered. 2 N hydrochloric acid was added to the mixture to adjust the pH to 3 and a little ethanol was added thereto. After crystallization, the mixture was filtered and the product was rinsed with water and then with ether and dried to obtain 102 mg of syn isomer of (6RS, 7RS) 7-[2-(2-amino-4-thiazolyl)-2-methoxyimino-acetamido]-8-oxo-4-thia-1-azabicyclo [4,2,0] oct-2-ene-2-carboxylic acid

Workup

  1. temperaturewas then cooled to room temperature
  2. filtrationwas then filtered
  3. washthe filter was rinsed with water
  4. additionA little ethanol was added to the filtrate which
  5. customwas then evaporated to dryness under reduced pressure
  6. customethanol and the mixture was again evaporated to dryness
  7. additionThe residue was added to 2 ml of a 1 M solution of sodium bicarbonate solution and 1.65 ml of water
  8. customto form a solution which
  9. filtrationwas then filtered
  10. addition2 N hydrochloric acid was added to the mixture
  11. additiona little ethanol was added
  12. customAfter crystallization
  13. filtrationthe mixture was filtered
  14. washthe product was rinsed with water
  15. dry with materialwith ether and dried

Sources & evidence

ORD record
ord-d4780927aeea42ae84fdfd86970e9e5b
Source dataset
uspto-grants-1984_10
Patent number
US04476124

Reaction notes

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