(2R,3S,5R,6R) 2-(N-Acetyl)carbamoyloxymethyl-6-amino2-methylpenam-3-carboxylic Acid p-Nitrobenzyl Ester → (2R,3S,5R,6R)2-(N-Acetyl)carbamoyloxymethyl-6-amino-2-methylpenam-3-carboxylic Acid

HRID 2295930Notes

Reaction equation

HRID 2295930 reaction equation
[N+](C1C=CC(C[O:9][C:10]([C@@H:12]2[N:16]3[C:17](=[O:20])[C@@H:18]([NH2:19])[C@H:15]3[S:14][C@:13]2([CH2:22][O:23][C:24](=[O:29])[NH:25][C:26](=[O:28])[CH3:27])[CH3:21])=[O:11])=CC=1)([O-])=O.[H][H]>[Pd].O>[C:26]([NH:25][C:24]([O:23][CH2:22][C@@:13]1([CH3:21])[C@H:12]([C:10]([OH:11])=[O:9])[N:16]2[C:17](=[O:20])[C@@H:18]([NH2:19])[C@H:15]2[S:14]1)=[O:29])(=[O:28])[CH3:27]

Participants

5

Reactant 2

HCID 57153220(2R,3S,5R,6R) 2-(N-Acetyl)carbamoyloxymethyl-6-amino2-methylpenam-3-carboxylic Acid p-Nitrobenzyl EsterHCID 178418361HCID 178418361, compound

Product 1

HCID 18598136(2R,3S,5R,6R)2-(N-Acetyl)carbamoyloxymethyl-6-amino-2-methylpenam-3-carboxylic AcidYield 65.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

To a prehydrogenated suspension of 10% palladium on carbon (0.83 gm), water-washed ethyl acetate (8.3 ml) and water (4.1 ml) was added (2R,3S,5R,6R) 2-(N-acetyl)carbamoyloxymethyl-6-amino-2-methylpenam-3-carboxylic acid p-nitrobenzyl ester (0.83 gm, 1.84 mmol). The mixture was shaken at 50 psi hydrogen pressure for 80 minutes and filtered through Dicalite-coated paper. The aqueous phase was separated, concentrated at reduced pressure to remove volatile solvent and gases, frozen and lyophilized. There was obtained 0.38 gm of the title compound as a white amorphous solid. Its nmr spectrum was consistent with the desired product.

Workup

  1. washwashed ethyl acetate (8.3 ml) and water (4.1 ml)
  2. filtrationfiltered through Dicalite-coated paper
  3. customThe aqueous phase was separated
  4. concentrationconcentrated at reduced pressure
  5. customto remove volatile solvent and gases
  6. temperaturefrozen

Sources & evidence

ORD record
ord-2be665adce594dda95339cb8c7a662f3
Source dataset
uspto-grants-1984_01
Patent number
US04426520

Reaction notes

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