Ethanol → HCID 67220766, compound

HRID 1024550Notes

Reaction equation

HRID 1024550 reaction equation
CC1C=C2N=C3C(=NC(NC3=O)=O)N(C[C@H](O)[C@H](O)[C@H](O)CO)C2=CC=1C.[F:28][C:29]1[C:34]([N+:35]([O-])=O)=[CH:33][C:32]([N:38]2[C:42](=[O:43])[N:41]([CH3:44])[N:40]=[N:39]2)=[C:31]([C@@H:45]2[CH2:47][C@H:46]2[C:48]([F:51])([F:50])[F:49])[CH:30]=1.CCO>[Pd].CC(O)=O>[NH2:35][C:34]1[C:29]([F:28])=[CH:30][C:31]([C@@H:45]2[CH2:47][C@H:46]2[C:48]([F:50])([F:49])[F:51])=[C:32]([N:38]2[C:42](=[O:43])[N:41]([CH3:44])[N:40]=[N:39]2)[CH:33]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 493570RiboflavinHCID 67217905HCID 67217905, compound

Product 1

HCID 67220766HCID 67220766, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

Palladium on charcoal, wet (Degussa grade E101; 29 mg) was added to a mixture of trans-1-(4-fluoro-2-(2-(trifluoromethyl)cyclopropyl)-5-nitrophenyl)-4-methyl-1H-tetrazol-5(4H)-one (145 mg, 0.46 mmol), EtOH (10 mL) and AcOH (75 μL) under nitrogen. The mixture was evacuated and filled with hydrogen—this procedure was repeated another two times. The mixture was hydrogenated at 30 psi for 7 days (topping-off the hydrogen if necessary). More Pd on charcoal, wet (Degussa grade E101; 15 mg) was added and the mixture hydrogenated at 30 psi for another 10 days (LC/MS was used to monitor the progression of the reaction over the 2 week experiment). After complete reaction, the mixture was filtered through a small plug of Celite and the filter cake washed with EtOH (3×10 mL). The filtrate was concentrated under vacuum (dry-loaded on to silica) and purified by column chromatography on silica gel using EtOAc/hexane (1:4 to 2:3) as eluent to give the product (117 mg, 89%) as a solid.

Workup

  1. customThe mixture was evacuated
  2. additionfilled with hydrogen—this procedure
  3. additionMore Pd on charcoal, wet (Degussa grade E101; 15 mg) was added
  4. waitthe mixture hydrogenated at 30 psi for another 10 days (LC/MS was used
  5. customthe progression of the reaction over the 2 week experiment)
  6. customAfter complete reaction
  7. filtrationthe mixture was filtered through a small plug of Celite
  8. washthe filter cake washed with EtOH (3×10 mL)
  9. concentrationThe filtrate was concentrated under vacuum (dry-loaded on to silica)
  10. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-9b8d9efcda8645c9bd5575e2c7066ff5
Source dataset
uspto-grants-2014_05
Patent number
US08722916B2

Reaction notes

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