tert-Butyl methylcarbamate → {4-[2-(4-Benzyloxy-2-oxo-2H-pyridin-1-yl)-ethyl]-benzyl}-methyl-carbamic Acid Tert-Butyl Ester

HRID 564161Notes

Reaction equation

HRID 564161 reaction equation
[C:1]([O:5][C:6](=[O:9])[NH:7][CH3:8])([CH3:4])([CH3:3])[CH3:2].[CH2:10]([O:17][C:18]1[CH:23]=[CH:22][N:21]([CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([CH2:32]Br)=[CH:28][CH:27]=2)[C:20](=[O:34])[CH:19]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C1COCC1.CCOC(C)=O.O>[C:1]([O:5][C:6](=[O:9])[N:7]([CH2:32][C:29]1[CH:30]=[CH:31][C:26]([CH2:25][CH2:24][N:21]2[CH:22]=[CH:23][C:18]([O:17][CH2:10][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)=[CH:19][C:20]2=[O:34])=[CH:27][CH:28]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 527635tert-Butyl methylcarbamateHCID 670065714-Benzyloxy-1-[2-(4-bromomethyl-phenyl)-ethyl]-1H-pyridin-2-one

Product 1

HCID 67006987{4-[2-(4-Benzyloxy-2-oxo-2H-pyridin-1-yl)-ethyl]-benzyl}-methyl-carbamic Acid Tert-Butyl Ester

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 49 mg (0.38 mmol) methyl-carbamic acid tert-butyl ester in 4.0 mL THF is added at RT 48 mg (0.43 mmol) potassium-tert-butylate. The reaction mixture is stirred 20 min at RT and then 100 mg (0.25 mmol) 4-benzyloxy-1-[2-(4-bromomethyl-phenyl)-ethyl]-1H-pyridin-2-one (example 1.1a) is added. The mixture is stirred additional 1 h at RT and is diluted with EtOAc and water. The layers are separated and the organic phase is washed with water, dried over MgSO4, filtered and the solvent is evaporated to afford the product.

Workup

  1. stirringThe mixture is stirred additional 1 h at RT
  2. customThe layers are separated
  3. washthe organic phase is washed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent is evaporated
  7. customto afford the product

Sources & evidence

ORD record
ord-c14760550b504f728e86167f77d97fb4
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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