Ethanol → HCID 131712879, compound

HRID 2199027Notes

Reaction equation

HRID 2199027 reaction equation
[CH2:1]([O:8][C:9]([CH2:11][S:12][C:13]1[CH2:14][C@@H:15]2[CH:32]([CH:33]([OH:35])[CH3:34])[C:31](=[O:36])[N:16]2[C:17]=1[C:18]([O:20]CC1C=CC([N+]([O-])=O)=CC=1)=[O:19])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C.C(=O)(O)[O-].[Na+:44]>O1CCOCC1.[Pd].O>[CH2:1]([O:8][C:9]([CH2:11][S:12][C:13]1[CH2:14][C@@H:15]2[CH:32]([CH:33]([OH:35])[CH3:34])[C:31](=[O:36])[N:16]2[C:17]=1[C:18]([O-:20])=[O:19])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[Na+:44]

Participants

7

Reactant 3

HCID 702EthanolHCID 516892Sodium BicarbonateHCID 131712881HCID 131712881, compound

Product 1

HCID 131712879HCID 131712879, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

A solution of p-nitrobenzyl 2-benzyloxycarbonylmethylthio-6-(1-hydroxy)ethyl-carbapen-2-em-3-carboxylate (7.1 mg, 0.014 mmol) in dioxane (0.84 ml) is treated with ethanol (0.07 ml), water (0.49 ml) containing sodium bicarbonate (1.4 mg, 0.017 mmol), and 10% palladium on charcoal (7.1 mg) and the mixture is hydrogenated at 40 psi for 30 minutes. The mixture is diluted to 3 ml with water and centrifuged to remove the catalyst which is washed with more water (2×1 ml). The combined aqueous solution is washed with ethylacetate (4×2 ml), filtered through a cotton plug, concentrated in vacuo to ca. 1 ml, and lyophilized to provide the title compound as a powder: UV (0.1 M pH 7 phosphate buffer) 300 nm; electrophoresis (0.05 M pH 7 phosphate buffer, 2 KV, 25 ma, 20 mins) gives a single bioactive zone migrating 3.5 cm toward the anode.

Workup

  1. customto remove the catalyst which
  2. washis washed with more water (2×1 ml)
  3. washThe combined aqueous solution is washed with ethylacetate (4×2 ml)
  4. filtrationfiltered through a cotton plug
  5. concentrationconcentrated in vacuo to ca. 1 ml

Sources & evidence

ORD record
ord-580d0f38029942b6820e83e8981940d6
Source dataset
uspto-grants-1982_11
Patent number
US04361512

Reaction notes

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