Dimethylformamide → HCID 86656340, compound

HRID 1942455Notes

Reaction equation

HRID 1942455 reaction equation
Br[C:2]1[C:20]([C:21]([N:23]([CH:37]([CH3:39])[CH3:38])[C@@H:24]2[CH2:29][CH2:28][CH2:27][N:26]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:25]2)=[O:22])=[CH:19][C:5]2[N:6]([CH2:13][CH2:14][CH2:15][CH2:16][O:17][CH3:18])[C:7](=[O:12])[C:8]([CH3:11])([CH3:10])[O:9][C:4]=2[CH:3]=1.C[O-].[Na+].CN([CH:46]=[O:47])C>O>[CH:37]([N:23]([C:21]([C:20]1[C:2]([O:47][CH3:46])=[CH:3][C:4]2[O:9][C:8]([CH3:11])([CH3:10])[C:7](=[O:12])[N:6]([CH2:13][CH2:14][CH2:15][CH2:16][O:17][CH3:18])[C:5]=2[CH:19]=1)=[O:22])[C@@H:24]1[CH2:29][CH2:28][CH2:27][N:26]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:25]1)([CH3:39])[CH3:38]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 10942334Sodium MethoxideHCID 86656341HCID 86656341, compound

Product 1

HCID 86656340HCID 86656340, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To tert-Butyl (3R)-3-[{[7-bromo-4-(4-methoxybutyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl]carbonyl}(isopropyl)amino]piperidine-1-carboxylate (500 mg) were added CuBr (59 mg), NaOMe (1M methanol solution) (16.4 ml) and DMF (5.5 ml), and the mixture was stirred at 100° C. for 15 hours. After the reaction was complete, water was added to the reaction solution, and the mixture was extracted with ethyl acetate solution. The obtained ethyl acetate solution was washed with water and a saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and concentrated. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/2) to give the title compound (240 mg) as a colorless liquid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate solution
  2. washThe obtained ethyl acetate solution was washed with water
  3. dry with materiala saturated aqueous sodium chloride solution, dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/2)

Sources & evidence

ORD record
ord-fa6627ba8aa447bdb0197abf1eba8744
Source dataset
uspto-grants-2013_03
Patent number
US08389511B2

Reaction notes

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