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

HRID 2091511Notes

Reaction equation

HRID 2091511 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 rt 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-1bca5c5f4d0945648290f2b9c12d472b
Source dataset
uspto-grants-2013_05
Patent number
US08440658B2

Reaction notes

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