Sodium Bicarbonate → Sodium 2-(2-acetoxy-2-methylaziridin-1-yl)-carbapen-2-em-3-carboxylate

HRID 329670Notes

Reaction equation

HRID 329670 reaction equation
[C:1]([O:4][C:5]1([CH3:29])[CH2:7][N:6]1[C:8]1[CH2:9][C@@H:10]2[CH2:27][C:26](=[O:28])[N:11]2[C:12]=1[C:13]([O:15]CC1C=CC([N+]([O-])=O)=CC=1)=[O:14])(=[O:3])[CH3:2].C(=O)(O)[O-].[Na+:34]>O1CCOCC1.O.C(O)C.[Pd]>[C:1]([O:4][C:5]1([CH3:29])[CH2:7][N:6]1[C:8]1[CH2:9][C@@H:10]2[CH2:27][C:26](=[O:28])[N:11]2[C:12]=1[C:13]([O-:15])=[O:14])(=[O:3])[CH3:2].[Na+:34]

Participants

7

Reactant 2

HCID 516892Sodium BicarbonateHCID 131715748p-Nitrobenzyl 2-(2-acetoxy-2-methylaziridin-1-yl)carbapen-2-em-3-carboxylate

Product 1

HCID 131715749Sodium 2-(2-acetoxy-2-methylaziridin-1-yl)-carbapen-2-em-3-carboxylate

Reagents, catalysts & solvents 4

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

Procedure

A solution of p-nitrobenzyl 2-(2-acetoxy-2-methyl-aziridin-1-yl)-carbapen-2-em-3-carboxylate (0.9 mg, 2.3 micromol) in dioxane (100 microliter), deionized water (60 microliter), absolute ethanol (8 microliter), and 0.5M aqueous sodium bicarbonate (5 microliter) was shaken with 10% (w/w) palladium on charcoal (1.1 mg) under hydrogen (50 psig) for 30 min. The mixture was centrifuged and the pellet washed with deionized water (3×100 microliter). The combined supernate and washes were extracted with ethyl acetate (3×0.5 ml) and concentrated under vacuum to provide 420 microliter of a solution of sodium 2-(2-acetoxy-2-methylaziridin-1-yl)-carbapen-2-em-3-carboxylate.

Workup

  1. washthe pellet washed with deionized water (3×100 microliter)
  2. extractionThe combined supernate and washes were extracted with ethyl acetate (3×0.5 ml)
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-b087e6cd17f14ad2a194e567228dfcc5
Source dataset
uspto-grants-1990_01
Patent number
US04892869

Reaction notes

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