HCID 57121265, compound → HCID 15117379, compound

HRID 1029688Notes

Reaction equation

HRID 1029688 reaction equation
C(OC([N:11]1[CH2:16][CH:15]=[C:14]([C:17]2[CH2:23][C@H:22]3[N:19]([C:20](=[O:27])[C@@H:21]3[C@H:24]([OH:26])[CH3:25])[C:18]=2[C:28]([O:30]CC2C=CC([N+]([O-])=O)=CC=2)=[O:29])[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.[H][H]>P([O-])([O-])([O-])=O.[Pd]>[OH:26][C@@H:24]([C@H:21]1[C:20](=[O:27])[N:19]2[C@@H:22]1[CH2:23][C:17]([CH:14]1[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]1)=[C:18]2[C:28]([OH:30])=[O:29])[CH3:25]

Participants

5

Reactant 2

HCID 57121265HCID 57121265, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15117379HCID 15117379, compoundYield 58.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1061PhosphateSolvent

Procedure

To a solution of 4-nitrobenzyl (5R,6S)-3-(1-benzyloxycarbonyl-1,2,3,6-tetrahydropyridin-4-yl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (500 mg) in 0.1M phosphate buffer (pH 6.93, 20 ml) was added 20% (W/W) palladium on carbon (50% wet) and the solution was stirred under atmospheric pressure of hydrogen at ambient temperature for 5 hours. The catalyst was filtered off and the filtrate was concentrated in vacuo to give a residual solution, which was chromatographed on "Diaion HP-20" (100 ml) eluting in turn with water and a mixture of water and acetone (50:1-20:1, V/V). The fractions containing the desired compound were collected and lyophilized to give (5R,6S)-6-[(1R)-1-hydroxyethyl]-7-oxo-3-(piperidin-4-yl)-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (150 mg).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. customto give a residual solution, which
  4. customwas chromatographed on "Diaion
  5. wash" (100 ml) eluting in turn with water
  6. additiona mixture of water and acetone (50:1-20:1, V/V)
  7. additionThe fractions containing the desired compound
  8. customwere collected

Sources & evidence

ORD record
ord-1f9e3461851e4197a85f7114b09312a6
Source dataset
uspto-grants-1992_04
Patent number
US05102877

Reaction notes

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