Diethyl Ether → HCID 70433336, compound

HRID 1583521Notes

Reaction equation

HRID 1583521 reaction equation
C1(OP([O-])(OC2C=CC=CC=2)=O)C=CC=CC=1.[NH2:18][C:19]1[CH:20]=[N+:21]([CH2:25][CH2:26][S:27][C:28]2[CH2:34][C@H:33]3[N:30]([C:31](=[O:38])[C@@H:32]3[C@H:35]([OH:37])[CH3:36])[C:29]=2[C:39]([O:41]CC2C=CC([N+]([O-])=O)=CC=2)=[O:40])[CH:22]=[CH:23][CH:24]=1.C1COCC1.CCOCC>P([O-])([O-])([O-])=O.[Pd]>[NH2:18][C:19]1[CH:20]=[N+:21]([CH2:25][CH2:26][S:27][C:28]2[CH2:34][C@H:33]3[N:30]([C:31](=[O:38])[C@@H:32]3[C@H:35]([OH:37])[CH3:36])[C:29]=2[C:39]([O-:41])=[O:40])[CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 8028TetrahydrofuranHCID 86740505HCID 86740505, compound

Product 1

HCID 70433336HCID 70433336, compoundYield 128.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1061PhosphateSolvent

Procedure

To a mixture of p-nitrobenzyl (5R, 6S)-3(2-(3-aminopyridinio)ethyl thio)-6-(1-(R)-hydroxyethyl)-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylate diphenylphosphate (0.730 g, 1.0 mmol) and 10% palladium-on-charcoal (0.7 g) in 25 mL of a phosphate buffer (0.05 m, pH 7.4) was added 8 mL of THF and 20 mL of ether. This mixture was then hydrogenated (Parr) at 40 psi for 1 h. The resulting mixture was filtered through a pad of Celite and the filter cake was washed with H2O and ether. The aqueous phase was separated, washed with ether (2x) and then residual volatiles were removed in vacuo. The aqueous solution was immediately applied to a C18 reverse-phase column which was eluted with H2O. Lyophilization of the relevant fractions afforded 0.45 g of an off-white solid. This material was repurified by reverse-phase hplc to give the desired product (0.123 g, 35%) as an ivory-colored solid.

Workup

  1. filtrationThe resulting mixture was filtered through a pad of Celite
  2. washthe filter cake was washed with H2O and ether
  3. customThe aqueous phase was separated
  4. washwashed with ether (2x)
  5. customresidual volatiles were removed in vacuo
  6. washwas eluted with H2O

Sources & evidence

ORD record
ord-6141172db50547dda2b059fcdf1f5841
Source dataset
uspto-grants-1985_11
Patent number
US04552696

Reaction notes

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