Dimethylformamide → HCID 86656346, compound

HRID 1942463Notes

Reaction equation

HRID 1942463 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[C:9]2[CH:10]=[C:11]([C:15]([N:17]([CH:31]([CH3:33])[CH3:32])[C@@H:18]3[CH2:23][CH2:22][CH2:21][N:20]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:19]3)=[O:16])[C:12]([CH3:14])=[CH:13][C:8]=2[O:7][C:6]([CH3:35])([CH3:34])[C:5]1=[O:36].[H-].[Na+].CN(C)C=O.[C:44](Cl)(=[O:47])[CH2:45][CH3:46]>O>[CH:31]([N:17]([C:15]([C:11]1[C:12]([CH3:14])=[CH:13][C:8]2[O:7][C:6]([CH3:34])([CH3:35])[C:5](=[O:36])[N:4]([CH2:3][CH2:2][O:1][C:44](=[O:47])[CH2:45][CH3:46])[C:9]=2[CH:10]=1)=[O:16])[C@@H:18]1[CH2:23][CH2:22][CH2:21][N:20]([C:24]([O:26][C:27]([CH3:29])([CH3:28])[CH3:30])=[O:25])[CH2:19]1)([CH3:32])[CH3:33]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 62324Propionyl chlorideHCID 67331844tert-butyl (3R)-3-[{[4-(2-hydroxyethyl)-2,2,7-trimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl]carbonyl}(isopropyl)amino]piperidine-1-carboxylate

Product 1

HCID 86656346HCID 86656346, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To tert-butyl (3R)-3-[{[4-(2-hydroxyethyl)-2,2,7-trimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl]carbonyl}(isopropyl)amino]piperidine-1-carboxylate (150 mg) were added sodium hydride (16 mg) and N,N-dimethylformamide (9 ml) under ice-cooling, and the mixture was stirred at room temperature for 30 minutes. Then, to the mixture was added propionic chloride (0.03 ml), and the mixture was further stirred at room temperature for 2 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 an 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 (110 mg) as a colorless liquid.

Workup

  1. temperaturecooling
  2. stirringthe mixture was further stirred at room temperature for 2 hours
  3. extractionthe mixture was extracted with ethyl acetate solution
  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 was purified by silica gel column chromatography (hexane/ethyl acetate=1/2)

Sources & evidence

ORD record
ord-6db2da52f8aa41fea3cc3752d7850bd8
Source dataset
uspto-grants-2013_03
Patent number
US08389511B2

Reaction notes

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