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

HRID 2059151Notes

Reaction equation

HRID 2059151 reaction equation
[N+](C1C=CC(C[O:9][C:10]([C@@H:12]2[N:16]3[C:17](=[O:30])[C@@H:18]([NH:19][C:20](=[O:29])[C@H:21]([NH2:28])[C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C@H:15]3[S:14][C@:13]2([CH2:32][O:33][C:34](=[O:39])[NH:35][C:36](=[O:38])[CH3:37])[CH3:31])=[O:11])=CC=1)([O-])=O.[H][H]>[Pd].O>[C:36]([NH:35][C:34]([O:33][CH2:32][C@@:13]1([CH3:31])[C@H:12]([C:10]([OH:11])=[O:9])[N:16]2[C:17](=[O:30])[C@@H:18]([NH:19][C:20](=[O:29])[C@H:21]([NH2:28])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C@H:15]2[S:14]1)=[O:39])(=[O:38])[CH3:37]

Participants

5

Reactant 2

HCID 70489758(2R,3S,5R,6R) 2-(N-Acetyl)carbamoyloxymethyl-6-[(R)-2-Amino-2-phenylacetamido]-2-methylpenam-3-carboxylic Acid p-Nitrobenzyl EsterHCID 178418361HCID 178418361, compound

Product 1

HCID 18598137(2R,3S,5R,6R) 2-(N-Acetyl)carbamoyloxymethyl-6-[(R)-2-amino-2-phenylacetamido]-2-methylpenam-3-carboxylic AcidYield 62.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

To a prehydrogenated suspension of 10% palladium on carbon (0.59 gm), water-washed ethyl acetate (6.0 ml) and water (3.0 ml) was added (2R,3S,5R,6R) 2-(N-acetyl)carbamoyloxymethyl-6-[(R)-2-amino-2-phenylacetamido]-2-methylpenam-3-carboxylic acid p-nitrobenzyl ester (0.59 gm. 1.06 mmol). The mixture was shaken at 50 psi hydrogen pressure for 3 hours at 25° and then 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 0.30 gm of the title compound as an amorphous solid. The purity was estimated from its nmr spectrum to be 60-70%.

Workup

  1. washwashed ethyl acetate (6.0 ml) and water (3.0 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-f7b4a0ddfcb64cfda33bbe28fbf7b476
Source dataset
uspto-grants-1982_03
Patent number
US04322347

Reaction notes

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