Sodium Bicarbonate → Sodium 2-amino-carbapen-2-em-3-carboxylate

HRID 2231695Notes

Reaction equation

HRID 2231695 reaction equation
[N:1]([C:4]1[CH2:5][C@@H:6]2[CH2:23][C:22](=[O:24])[N:7]2[C:8]=1[C:9]([O:11]CC1C=CC([N+]([O-])=O)=CC=1)=[O:10])=[N+]=[N-].C(=O)(O)[O-].[Na+:29]>O1CCOCC1.O.C(O)C.[Pd]>[NH2:1][C:4]1[CH2:5][C@@H:6]2[CH2:23][C:22](=[O:24])[N:7]2[C:8]=1[C:9]([O-:11])=[O:10].[Na+:29]

Participants

7

Reactant 2

HCID 516892Sodium BicarbonateHCID 131715741p-Nitrobenzyl 2-azidocarbapen-2-em-3-carboxylate

Product 1

HCID 131715744Sodium 2-amino-carbapen-2-em-3-carboxylate

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of p-nitrobenzyl 2-azido-carbapen-2-em-3-carboxylate (3.3 mg, 10 micromol) in dioxane (300 microliter), deionized water (180 microliter), absolute ethanol (25 μl), and aqueous sodium bicarbonate solution (20 microliter of 0.5M) was shaken with 10% palladium on charcoal (3.3 mg) under hydrogen (50 psig) at ambient temperature for 40 min. The mixture was centrifuged and the pellet was washed with deionzed water (3×0.3 ml). The combined supernates were extracted with ethyl acetate (3×0.4 ml) and lyophilized to provide sodium 2-amino-carbapen-2-em-3-carboxylate.

Workup

  1. washthe pellet was washed with deionzed water (3×0.3 ml)
  2. extractionThe combined supernates were extracted with ethyl acetate (3×0.4 ml)

Sources & evidence

ORD record
ord-5847487961594fcb90d54a6ea5ac392d
Source dataset
uspto-grants-1988_11
Patent number
US04783453

Reaction notes

Loading…