Acetic Acid → HCID 20429022, compound

HRID 615114Notes

Reaction equation

HRID 615114 reaction equation
[O:1]([CH2:8][C:9]([NH:11][CH:12]1[C:19](=[O:20])[N:18]2[CH:13]1[S:14][CH2:15][NH:16][CH:17]2[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=[O:33])C.[SH-].[Na+]>O>[O:1]([CH2:8][C:9]([NH:11][CH:12]1[C:19](=[O:20])[N:18]2[CH:13]1[S:14][CH2:15][N:16]([OH:33])[CH:17]2[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 28015Sodium hydrosulfideHCID 14230825Benzyl 7-phenoxyacetamido-8-oxo-5-thia-1,3-diazabicyclo[4,2,0]octane-2-carboxylate

Product 1

HCID 20429022HCID 20429022, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of benzyl 7-phenoxyacetamido-8-oxo-5-thia-1,3-diazabicyclo[4,2,0]octane-2-carboxylate (635 mg.) and cupric sulfate pentahydrate (75 mg.) in a mixed solution of acetic acid (4 ml.) and water (0.4 ml.) was stirred at room temperature. After stirring for 100 minutes, an additional cupric sulfate pentahydrate (300 mg.) was added thereto and the mixture was stirred for additional 1.5 hours. The reaction mixture was cooled to 10° C. and sodium bisulfide (86 mg.) was added thereto. The resultant mixture was filtered through a pad of Celite and the filtrate was concentrated. The residue was taken up into ethyl acetate, washed with a dilute aqueous solution of sodium bicarbonate and an aqueous solution of sodium chloride. Drying over magnesium sulfate and removal of the solvent gave a residue (648 mg.), which was chromatographed on silica gel (20 g.) with a mixed solvent of benzene and ethyl acetate (5:1 to 2:1 by volume) to give an oil (307 mg.), which was crystallized from diethyl ether to afford benzyl 7-phenoxyacetamido-8-oxo-3-hydroxy-5-thia-1,3-diazabicyclo[4,2,0]octane-2-carboxylate (300 mg.), mp 184°-186° C.

Workup

  1. stirringAfter stirring for 100 minutes
  2. stirringthe mixture was stirred for additional 1.5 hours
  3. temperatureThe reaction mixture was cooled to 10° C.
  4. filtrationThe resultant mixture was filtered through a pad of Celite
  5. concentrationthe filtrate was concentrated
  6. washwashed with a dilute aqueous solution of sodium bicarbonate
  7. dry with materialDrying over magnesium sulfate and removal of the solvent
  8. customgave a residue (648 mg.), which
  9. customwas chromatographed on silica gel (20 g.) with a mixed solvent of benzene and ethyl acetate (5:1 to 2:1 by volume)
  10. customto give an oil (307 mg.), which
  11. customwas crystallized from diethyl ether

Sources & evidence

ORD record
ord-5acf860f84704e7fb6a0f4529ba821b2
Source dataset
uspto-grants-1985_02
Patent number
US04497738

Reaction notes

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