Sodium Bicarbonate → (2R,3S,5R,6R) 2-(N-Acetyl)carbamoyloxymethyl-2-methyl-6-phenoxyacetamidopenam-3-carboxylic Acid

HRID 1758820Notes

Reaction equation

HRID 1758820 reaction equation
C(=O)(O)[O-].[Na+].[N+](C1C=CC(C[O:14][C:15]([C@@H:17]2[N:21]3[C:22](=[O:35])[C@@H:23]([NH:24][C:25](=[O:34])[CH2:26][O:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C@H:20]3[S:19][C@:18]2([CH2:37][O:38][C:39](=[O:44])[NH:40][C:41](=[O:43])[CH3:42])[CH3:36])=[O:16])=CC=1)([O-])=O.[H][H]>[Pd].C(OCC)(=O)C>[C:41]([NH:40][C:39]([O:38][CH2:37][C@@:18]1([CH3:36])[C@H:17]([C:15]([OH:16])=[O:14])[N:21]2[C:22](=[O:35])[C@@H:23]([NH:24][C:25](=[O:34])[CH2:26][O:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C@H:20]2[S:19]1)=[O:44])(=[O:43])[CH3:42]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 12817532(2R,3S,5R,6R) 2-(N-acetyl)carbamoyloxymethyl-2-methyl-6-phenoxyacetamidopenam-3-carboxylic acid p-nitrobenzyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 18598135(2R,3S,5R,6R) 2-(N-Acetyl)carbamoyloxymethyl-2-methyl-6-phenoxyacetamidopenam-3-carboxylic AcidYield 87%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 10% palladium on charcoal (400 mg) in ethyl acetate (40 ml) and aqueous 0.5% sodium bicarbonate was prehydrogenated and charged with (2R,3S,5R,6R) 2-(N-acetyl)carbamoyloxymethyl-2-methyl-6-phenoxyacetamidopenam-3-carboxylic acid p-nitrobenzyl ester (400 mg 0.68 mmol). The whole was shaken at 50 psi hydrogen pressure for 30 minutes and polish filtered. The aqueous was washed with ethyl acetate (20 ml), combined with a back extract of H2O (20 ml), overlayed with ethyl acetate (25 ml) and adjusted to pH 2.9 with 35% sulfuric acid. The layers were separated and the rich organic phase was washed with water (20 ml), combined with a back extract (EtOAc, 20 ml), dried (4A sieves), polish filtered and concentrated in vacuo to a colorless foam (270 mg) in 87% yield: nmr 100 MHz (CDCl3 --D2O) ppm 7.32 (2, m, m-phenyl H's) 6.96 (3, m, o,p-phenyl H's), 5.59 (2, br s, mag. equiv. C5,C6 --H's), 4.79 (1, s, C3 --H), 4.59 ##STR66## 4.08 (m, AB of C2 --CH2O), 2.25 ##STR67## and 1.58 (3, s, C3 --Me) with small ethyl acetate impurity.

Workup

  1. filtrationpolish filtered
  2. washThe aqueous was washed with ethyl acetate (20 ml)
  3. extractiona back extract of H2O (20 ml), overlayed with ethyl acetate (25 ml)
  4. customThe layers were separated
  5. washthe rich organic phase was washed with water (20 ml)
  6. extractionextract (EtOAc, 20 ml)
  7. dry with materialdried (4A sieves), polish
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo to a colorless foam (270 mg) in 87% yield

Sources & evidence

ORD record
ord-6a7d3d357d9f47cc9159c40b4b496e75
Source dataset
uspto-grants-1983_02
Patent number
US04374982

Reaction notes

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