Hydrochloric Acid → HCID 58049367, compound

HRID 467966Notes

Reaction equation

HRID 467966 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]([N:9]([CH:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[C@H:10]([C:23](OC)=[O:24])[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]([F:22])([F:21])[F:20])[CH:13]=2)=[O:8])[N:4]=[CH:3]1.[BH4-].[Na+].Cl.O>C(O)C>[OH:24][CH2:23][CH:10]([N:9]([CH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1)[C:7]([C:5]1[N:4]=[CH:3][N:2]([CH3:1])[CH:6]=1)=[O:8])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]([F:22])([F:21])[F:20])[CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 66670233HCID 66670233, compound

Product 1

HCID 58049367HCID 58049367, compoundYield 9.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of methyl N-[(1-methyl-1H-imidazol-4-yl)carbonyl]-N-(tetrahydro-2H-pyran-4-yl)-3-(trifluoromethoxy)phenylalaninate (55 mg) in ethanol (2.2 mL), sodium borohydride (23 mg) was added and the resulting mixture was heated under reflux for 3 hours. To the ice-cooled reaction mixture, 1 M HCl was added dropwise and the resulting mixture was stirred for 30 minutes at room temperature. After adding water, the mixture was subjected to extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate. After filtering off the desiccant, the filtrate was concentrated under reduced pressure and the resulting residue was purified by TLC (silica gel plate; chloroform/methanol=10:1) and column chromatography (NH silica gel cartridge; chloroform) to give the titled compound (4.9 mg).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 3 hours
  3. additionwas added dropwise
  4. extractionthe mixture was subjected to extraction with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationAfter filtering off the desiccant
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customthe resulting residue was purified by TLC (silica gel plate; chloroform/methanol=10:1) and column chromatography (NH silica gel cartridge; chloroform)

Sources & evidence

ORD record
ord-a49dd020741d4142aae645dc5de89337
Source dataset
uspto-grants-2014_01
Patent number
US08623898B2

Reaction notes

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