Sodium Bicarbonate → HCID 23708852, compound

HRID 1788845Notes

Reaction equation

HRID 1788845 reaction equation
[F:1][C:2]1[CH:28]=[CH:27][C:5]([O:6][C:7]2[S:13][CH:12]3[N:9]([CH2:10][CH2:11]3)[C:8]=2[C:14]([O:16]CC2C=CC([N+]([O-])=O)=CC=2)=[O:15])=[CH:4][CH:3]=1.C(=O)(O)[O-:30].[Na+:33]>O1CCOCC1.O.[Pd]>[F:1][C:2]1[CH:28]=[CH:27][C:5]([O:6][C:7]2[S:13][CH:12]3[N:9]([C:10](=[O:30])[CH2:11]3)[C:8]=2[C:14]([O-:16])=[O:15])=[CH:4][CH:3]=1.[Na+:33]

Participants

6

Reactant 2

HCID 516892Sodium BicarbonateHCID 20190014HCID 20190014, compound

Product 1

HCID 23708852HCID 23708852, compoundYield 95.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of a solution of 500 mg of 4-nitrobenzyl 3-(4-fluorophenoxy)-4-thia-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate in dioxan and 101 mg of sodium bicarbonate in water, and 10% palladium/charcoal was hydrogenated at 50 psi at 25° for 60 minutes. Then the reaction mixture was filtered through Celite, and then lyophilised to yield 348 mg of the title compound as a pale yellow crystalline solid (95% of the theoretical yield).

Workup

  1. filtrationThen the reaction mixture was filtered through Celite

Sources & evidence

ORD record
ord-bbae89eeb1164984848e253d3e573545
Source dataset
uspto-grants-1987_08
Patent number
US04684640

Reaction notes

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