Methyl chloroformate → Methyl 3-(2-((tert-butoxycarbonyl)amino)propan-2-yl)benzoate

HRID 64438Notes

Reaction equation

HRID 64438 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13](Br)[CH:12]=1)([CH3:10])[CH3:9])([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.CCCCCC.Cl[C:31]([O:33][CH3:34])=[O:32].[Cl-].[NH4+]>C1COCC1.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:7][C:8]([C:11]1[CH:12]=[C:13]([CH:14]=[CH:15][CH:16]=1)[C:31]([O:33][CH3:34])=[O:32])([CH3:10])[CH3:9])=[O:18])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 6586Methyl chloroformateHCID 25517Ammonium ChlorideHCID 53256542tert-Butyl (2-(3-bromophenyl)propan-2-yl)carbamateHCID 178418244HCID 178418244, compound

Product 1

HCID 86713455Methyl 3-(2-((tert-butoxycarbonyl)amino)propan-2-yl)benzoate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 850 mg of tert-butyl[2-(3-bromophenyl)propan-2-yl]carbamate in 8.5 ml of THF was added 4.1 ml of a 1.65 M n-butyllithium/hexane solution at −78° C., followed by stirring at the same temperature for 30 minutes. Then, 0.85 ml of methyl chloroformate was added dropwise thereto at −78° C., followed by stirring at the same temperature for 1 hour. To the reaction mixture were added a saturated aqueous ammonium chloride solution and ethyl acetate to carry out a layer separation operation. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 199 mg of methyl 3-{2-[(tert-butoxycarbonyl)amino]propan-2-yl}benzoate.

Workup

  1. customat −78° C.
  2. stirringby stirring at the same temperature for 1 hour
  3. customa layer separation operation
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1c071cfd6fc941398f6146ea1e35df76
Source dataset
uspto-grants-2016_09
Patent number
US09447090B2

Reaction notes

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