Diethyl Ether → HCID 70433336, compound

HRID 236055Notes

Reaction equation

HRID 236055 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 (2×) 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 relevent 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 (2×)
  5. customresidual volatiles were removed in vacuo
  6. washwas eluted with H2O

Sources & evidence

ORD record
ord-4abb8a2625684f07b8d3acdfaae8d935
Source dataset
uspto-grants-1987_02
Patent number
US04642341

Reaction notes

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