Ethanol → sodium (5R,6S)-2-amino-6-[(R)-1-hydoxyethyl]carbapen-2-em-3-carboxylate

HRID 1762681Notes

Reaction equation

HRID 1762681 reaction equation
[N:1]([C:4]1[CH2:5][C@@H:6]2[C@@H:23]([C@H:24]([OH:26])[CH3:25])[C:22](=[O:27])[N:7]2[C:8]=1[C:9]([O:11]CC1C=CC([N+]([O-])=O)=CC=1)=[O:10])=[N+]=[N-].O1CCCC1.C(O)C.C(=O)(O)[O-].[Na+:40]>[Pd].O>[NH2:1][C:4]1[CH2:5][C@@H:6]2[C@@H:23]([C@H:24]([OH:26])[CH3:25])[C:22](=[O:27])[N:7]2[C:8]=1[C:9]([O-:11])=[O:10].[Na+:40]

Participants

7

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 14329106p-nitrobenzyl (5R,6S)-2-azido-6-[(R)-1-hydroxyethyl]-carbapen-2-em-3-carboxylate

Product 1

HCID 23718245sodium (5R,6S)-2-amino-6-[(R)-1-hydoxyethyl]carbapen-2-em-3-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A mixture of p-nitrobenzyl (5R,6S)-2-azido-6-[(R)-1-hydroxyethyl]carbapen-2-em-3-carboxylate (75 mg, 0.2 mmol), tetrahydrofuran (14 ml), ethanol (14 ml), deionized water (11 ml) containing sodium bicarbonate (16.8 mg, 0.2 mmol), and 10% palladium on carbon (75 mg) is shaken under hydrogen (45 psi) at ambient temperature for 2 hours. The mixture is filtered through a celite pad to remove the catalyst which is washed with water. The combined filtrate and wash is extracted with three portions of diethyl ether, concentrated under vacuum to about 10 ml volume, and lyophilized to afford sodium (5R,6S)-2-amino-6-[(R)-1-hydoxyethyl]carbapen-2-em-3-carboxylate.

Workup

  1. filtrationThe mixture is filtered through a celite pad
  2. customto remove the catalyst which
  3. washis washed with water
  4. washThe combined filtrate and wash
  5. extractionis extracted with three portions of diethyl ether
  6. concentrationconcentrated under vacuum to about 10 ml volume

Sources & evidence

ORD record
ord-7f598e2c8ad54a858a895161609a19d9
Source dataset
uspto-grants-1989_05
Patent number
US04833167

Reaction notes

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