Tert-butyl 1-(methoxy(methyl)amino)-3,3-dimethyl-1-oxobutan-2-ylcarbamate → 2-(Boc-amino)-2-t-butyl-1-(4-chlorophenyl)ethanone

HRID 535775Notes

Reaction equation

HRID 535775 reaction equation
CON(C)[C:4](=[O:18])[CH:5]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[C:6]([CH3:9])([CH3:8])[CH3:7].[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([Mg]Br)=[CH:23][CH:22]=1>C1COCC1>[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([C:4](=[O:18])[CH:5]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[C:6]([CH3:7])([CH3:8])[CH3:9])=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 21305336Tert-butyl 1-(methoxy(methyl)amino)-3,3-dimethyl-1-oxobutan-2-ylcarbamateHCID 178478191HCID 178478191, compound

Product 1

HCID 684053282-(Boc-amino)-2-t-butyl-1-(4-chlorophenyl)ethanoneYield 25%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl 1-(methoxy(methyl)amino)-3,3-dimethyl-1-oxobutan-2-ylcarbamate (Example 1, 466 mg, 1.70 mmol) was dissolved in dry THF (10 mL). (4-Chlorophenyl)magnesium bromide (CAS 873-77-8, 1.0 M in THF, 6.79 mL, 6.79 mmol) was then added dropwise at rt. After stirring at rt overnight the reaction was quenched with NH4Cl and extracted with EtOAc (2×50 mL). The combined organic phases were washed once with water, dried over MgSO4 and filtered. After removal of the solvent the product was purified on a silica gel column eluted with heptane:EtOAc 10-20% to give tert-butyl 1-(4-chlorophenyl)-3,3-dimethyl-1-oxobutan-2-ylcarbamate (137 mg, 25%).

Workup

  1. customwas quenched with NH4Cl
  2. extractionextracted with EtOAc (2×50 mL)
  3. washThe combined organic phases were washed once with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customAfter removal of the solvent the product
  7. customwas purified on a silica gel column
  8. washeluted with heptane

Sources & evidence

ORD record
ord-19c2c6cb5faf45c58eac38685ba237ab
Source dataset
uspto-grants-2014_10
Patent number
US08859556B2

Reaction notes

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