Water → HCID 58691116, compound

HRID 2376672Notes

Reaction equation

HRID 2376672 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH2:16][C@H:15]3[N:12]([C:13](=[O:20])[C@@H:14]3[C@H:17]([OH:19])[CH3:18])[C:11]=2[C:21]([O:23]CC2C=CC([N+]([O-])=O)=CC=2)=[O:22])=[CH:6][CH:5]=1)[CH3:2].C(=O)([O-])O.[Na+:38].O.[H][H]>C1COCC1.[C].[Pd]>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH2:16][C@H:15]3[N:12]([C:13](=[O:20])[C@@H:14]3[C@H:17]([OH:19])[CH3:18])[C:11]=2[C:21]([O-:23])=[O:22])=[CH:6][CH:5]=1)[CH3:2].[Na+:38]

Participants

7

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 86607075HCID 86607075, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58691116HCID 58691116, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4-Nitrobenzyl (5R,6S)-3-(4-ethoxyphenyl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (1.39 g) prepared in accordance to the method described in Tetrahedron Letters, 34, 3211-3214 (1993)] was dissolved in THF (28 mL), and thereto were added under ice cooling sodium hydrogencarbonate in ion-exchange water (28 mL), and 10% palladium-carbon [50% water] (0.14 g). Then the atmosphere was changed with a hydrogen gas, and the mixture was stirred at the same temperature for 3 hours. After filtration of the insoluble materials with Celite, to the filtrate was added chloroform (80 mL). The organic layer was separated, and extracted with ion-exchange water (20 mL). The organic solvent in the aqueous solution separated and extracted was removed over one hour period in vacuo, purified with C18 reverse column chromatography (Wakosil C18 reverse column, mobile phase; ion-exchange water/THF) and lyophilized to give sodium (5R,6S)-3-(4-ethoxyphenyl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (0.44 g, yield 42%).

Workup

  1. additionwere added under ice
  2. filtrationAfter filtration of the insoluble materials with Celite
  3. additionto the filtrate was added chloroform (80 mL)
  4. customThe organic layer was separated
  5. extractionextracted with ion-exchange water (20 mL)
  6. customThe organic solvent in the aqueous solution separated
  7. extractionextracted
  8. customwas removed over one hour period in vacuo
  9. custompurified with C18 reverse column chromatography (Wakosil C18 reverse column, mobile phase; ion-exchange water/THF)

Sources & evidence

ORD record
ord-d477962f649b44f1b94631ad6d84aa17
Source dataset
uspto-grants-2008_12
Patent number
US07468364B2

Reaction notes

Loading…