Methyl chloroformate → (S)-methyl 3,3-dimethylbutan-2-yl(3-(4-fluorophenyl)-3-oxopropyl)carbamate

HRID 403577Notes

Reaction equation

HRID 403577 reaction equation
[CH3:1][C:2]([CH3:18])([CH3:17])[C@@H:3]([NH:5][CH2:6][CH2:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1)=[O:9])[CH3:4].C([O-])([O-])=O.[K+].[K+].Cl[C:26]([O:28][CH3:29])=[O:27]>C(Cl)Cl>[CH3:18][C:2]([CH3:17])([CH3:1])[C@@H:3]([N:5]([CH2:6][CH2:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1)=[O:9])[C:26](=[O:27])[O:28][CH3:29])[CH3:4]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 11430Potassium CarbonateHCID 58485266(S)-3-(3,3-dimethylbutan-2-ylamino)-1-(4-fluorophenyl)propan-1-one

Product 1

HCID 58485254(S)-methyl 3,3-dimethylbutan-2-yl(3-(4-fluorophenyl)-3-oxopropyl)carbamateYield 81.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-3-(3,3-dimethylbutan-2-ylamino)-1-(4-fluorophenyl)propan-1-one (2.00 g, 7.97 mmol) and K2CO3 (3.30 g, 23.9 mmol) in CH2Cl2 (100 mL) was added methyl chloroformate (2.25 g, 23.9 mmol) dropwise at 0° C., and the reaction mixture was stirred at it overnight. The solution was filtered, and the filtrate was concentrated to give the crude product, which was purified by chromatography to afford (S)-methyl 3,3-dimethylbutan-2-yl(3-(4-fluorophenyl)-3-oxopropyl)carbamate (2.0 g, 81%). 1H NMR (CDCl3): 0.92 (s, 9H), 1.12-1.21 (d, 3H), 3.02-3.11 (m, 1H), 3.27-3.49 (m, 1H), 3.66 (s, 3H), 3.98-4.23 (m, 1H), 7.06-7.17 (m, 2H), 7.92-8.08 (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-acf1e8fba2de459ba52946afb5f302d2
Source dataset
uspto-grants-2014_06
Patent number
US08748444B2

Reaction notes

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