Methyl chloroformate → HCID 58109706, compound

HRID 2037409Notes

Reaction equation

HRID 2037409 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][CH2:9][CH2:10][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:12])[CH:5]=[CH:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].Cl[C:26]([O:28][CH3:29])=[O:27]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([N:8]([CH2:9][CH2:10][C:11](=[O:12])[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:26](=[O:27])[O:28][CH3:29])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 11430Potassium CarbonateHCID 58109514HCID 58109514, compound

Product 1

HCID 58109706HCID 58109706, compoundYield 280.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of 3-(3-bromophenylamino)-1-phenylpropan-1-one (0.03 mol) in anhydrous THF (30 mL) was added K2CO3 (0.06 mol) and methyl chloroformate (0.033 mol) at 0° C. under N2 atmosphere. Then the reaction mixture was stirred at rt for 2 h. The resulting mixture was filtered and the filtrate was concentrated. The residue was washed with H2O, 1N HCl and brine and then extracted with EtOAc. The combined organic layers were concentrated to give crude product, which was purified by column chromatography to afford methyl 3-bromophenyl(3-oxo-3-phenylpropyl)carbamate (30.5 g, 95%). 1H NMR (400 MHz, CDCl3): δ=3.22 (m, 2H), 3.62 (s, 3H), 4.02 (m, 2H), 7.05-7.20 (m, 2H), 7.3-7.5 (m, 4H), 7.8 (m, 1H).

Workup

  1. filtrationThe resulting mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. washThe residue was washed with H2O, 1N HCl and brine
  4. extractionextracted with EtOAc
  5. concentrationThe combined organic layers were concentrated
  6. customto give crude product, which
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-ad11d38cdcba417fa186fad7dbf47dfd
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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