Methyl chloroformate → HCID 58485273, compound

HRID 2091528Notes

Reaction equation

HRID 2091528 reaction equation
[C:1]([NH:5][CH2:6][CH2:7][C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:9])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].Cl[C:23]([O:25][CH3:26])=[O:24]>C(Cl)Cl>[C:1]([N:5]([CH2:6][CH2:7][C:8](=[O:9])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:23](=[O:24])[O:25][CH3:26])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 11430Potassium CarbonateHCID 423813HCID 423813, compound

Product 1

HCID 58485273HCID 58485273, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(tert-butylamino)-1-phenylpropan-1-one (5.80 g, 0.028 mol) and K2CO3 (7.73 g, 0.056 mol) in CH2Cl2 (100 mL) was added dropwise methyl chloroformate (7.98 g, 0.085 mol) at 0° C., and the reaction mixture was stirred at rt overnight. The solution was filtered. The filtrate was concentrated to give the crude product, which was purified by chromatography to afford methyl tert-butyl(3-oxo-3-phenylpropyl)carbamate (5.09 g, 69%). 1H NMR (CDCl3): 1.43 (s, 9H), 3.16-3.21 (m, 2H), 3.62 (s, 3H), 3.60-3.72 (m, 2H), 7.2-7.49 (m, 2H), 7.51-7.59 (m, 1H), 7.93-7.98 (m, 2H).

Workup

  1. filtrationThe solution was filtered
  2. concentrationThe filtrate was concentrated
  3. customto give the crude product, which
  4. customwas purified by chromatography

Sources & evidence

ORD record
ord-78899faba4814544bcd86d73ec8c03dc
Source dataset
uspto-grants-2013_05
Patent number
US08440658B2

Reaction notes

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