Methanol → HCID 67332078, compound

HRID 1942457Notes

Reaction equation

HRID 1942457 reaction equation
C([O:3][C:4](=[O:43])[CH2:5][CH2:6][N:7]1[C:12]2[CH:13]=[C:14]([C:21]([N:23]([CH:37]([CH3:39])[CH3:38])[C@@H:24]3[CH2:29][CH2:28][CH2:27][N:26]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:25]3)=[O:22])[C:15]([C:17]([F:20])([F:19])[F:18])=[CH:16][C:11]=2[O:10][C:9]([CH3:41])([CH3:40])[C:8]1=[O:42])C.[OH-].[Na+].CO>C1COCC1>[C:33]([O:32][C:30]([N:26]1[CH2:27][CH2:28][CH2:29][C@@H:24]([N:23]([CH:37]([CH3:39])[CH3:38])[C:21]([C:14]2[C:15]([C:17]([F:18])([F:20])[F:19])=[CH:16][C:11]3[O:10][C:9]([CH3:40])([CH3:41])[C:8](=[O:42])[N:7]([CH2:6][CH2:5][C:4]([OH:43])=[O:3])[C:12]=3[CH:13]=2)=[O:22])[CH2:25]1)=[O:31])([CH3:34])([CH3:35])[CH3:36]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 67330942HCID 67330942, compound

Product 1

HCID 67332078HCID 67332078, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To tert-butyl (3R)-3-[{[4-(3-ethoxy-3-oxopropyl)-2,2-dimethyl-3-oxo-7-(trifluoromethyl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]carbonyl}(isopropyl)amino]piperidine-1-carboxylate (350 mg) were added a 2N NaOH aqueous solution (5 ml), MeOH (5 ml) and THF (5 ml), and the mixture was stirred at room temperature for 2 hours. After the reaction was complete, the solvent was concentrated, and thereto was added dropwise a 2N aqueous hydrochloric acid solution. The precipitated crystals were extracted with ethyl acetate. The obtained ethyl acetate solution was washed with water and an aqueous sodium chloride solution, dried over magnesium sulfate, filtered and concentrated. The obtained residue (260 mg) was used in the subsequent reaction without a further treatment.

Workup

  1. concentrationthe solvent was concentrated
  2. additionwas added dropwise a 2N aqueous hydrochloric acid solution
  3. extractionThe precipitated crystals were extracted with ethyl acetate
  4. washThe obtained ethyl acetate solution was washed with water
  5. dry with materialan aqueous sodium chloride solution, dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe obtained residue (260 mg) was used in the subsequent reaction without a further treatment

Sources & evidence

ORD record
ord-95102f863b614a469f9d51a881357656
Source dataset
uspto-grants-2013_03
Patent number
US08389511B2

Reaction notes

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