Methanol → HCID 59771032, compound

HRID 2426271Notes

Reaction equation

HRID 2426271 reaction equation
C(OC([NH:11][C@@H:12]1[CH2:27][N:16]2[C:17](=[O:26])[C:18]([OH:25])=[C:19]([C:21]([O:23]C)=O)[N:20]=[C:15]2[CH2:14][CH2:13]1)=O)C1C=CC=CC=1.CO.[F:30][C:31]1[CH:38]=[CH:37][C:34]([CH2:35][NH2:36])=[CH:33][CH:32]=1>>[NH2:11][C@@H:12]1[CH2:27][N:16]2[C:17](=[O:26])[C:18]([OH:25])=[C:19]([C:21]([NH:36][CH2:35][C:34]3[CH:37]=[CH:38][C:31]([F:30])=[CH:32][CH:33]=3)=[O:23])[N:20]=[C:15]2[CH2:14][CH2:13]1

Participants

4

Reactant 3

HCID 887MethanolHCID 673264-FluorobenzylamineHCID 67148497HCID 67148497, compound

Product 1

HCID 59771032HCID 59771032, compound

Procedure

The product from Step 2 was dissolved in MeOH (6 mmol), p-fluorobenzylamine (2.0 eq) was added and the mixture was stirred at reflux for 6 hours. The solvent was removed under reduced pressure and the residue was diluted with ethyl acetate. The organic phase was washed with 1N HCl, brine, dried over Na2SO4, filtered and concentrated to dryness under vacuum. To the resulting crude MeOH was added (20 ml/mmol) and the mixture was hydrogenated at atm pressure on 10% (w/w) Pd/C over night. After filtration of the catalyst, solvent was evaporated to give a crude that was purified by preparative RP-HPLC (Symmetry Column C18, 5 μm, 19×100 mm, gradient of CH3CN/H2O+0.01% TFA).

Workup

  1. temperatureat reflux for 6 hours
  2. customThe solvent was removed under reduced pressure
  3. additionthe residue was diluted with ethyl acetate
  4. washThe organic phase was washed with 1N HCl, brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under vacuum
  8. additionTo the resulting crude MeOH was added (20 ml/mmol)
  9. waitthe mixture was hydrogenated at atm pressure on 10% (w/w) Pd/C over night
  10. filtrationAfter filtration of the catalyst, solvent
  11. customwas evaporated
  12. customto give a crude that
  13. customwas purified by preparative RP-HPLC (Symmetry Column C18, 5 μm, 19×100 mm, gradient of CH3CN/H2O+0.01% TFA)

Sources & evidence

ORD record
ord-d33b5caec761418eb1ba7bb114b0791c
Source dataset
uspto-grants-2011_06
Patent number
US07968553B2

Reaction notes

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