Methyl chloroformate → HCID 58109666, compound

HRID 2037523Notes

Reaction equation

HRID 2037523 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][CH2:11][CH2:12][C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[F:21])=[O:14])[CH3:9])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[C:28](Cl)(=[O:31])[O:29][CH3:30]>CC#N>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]([CH2:11][CH2:12][C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[F:21])=[O:14])[C:28](=[O:31])[O:29][CH3:30])[CH3:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 11430Potassium CarbonateHCID 59635692(S)-3-(1-(4-bromophenyl)ethylamino)-1-(2-fluorophenyl)propan-1-one

Product 1

HCID 58109666HCID 58109666, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (S)-3-(1-(4-bromophenyl)ethylamino)-1-(2-fluorophenyl)propan-1-one (500 mg, 1.43 mmol) in anhydrous CH3CN (15 mL) was added K2CO3 and methyl carbonochloridate (403 mg, 4.29 mmol), and the mixture was stirred at rt for 2 h. The solution was concentrate, and the residue was purified by preparative TLC to afford (S)-methyl 1-(4-bromophenyl)ethyl(3-(2-fluorophenyl)-3-oxopropyl)carbamate (400 mg, 70%). 1H NMR (CDCl3): δ=1.50 (m, 3H), 3.00 (m, 2H), 3.36 (m, 2H), 3.78 (m, 3H), 5.40 (m, 1H), 7.11 (m, 4H), 7.28-7.50 (m, 3H), 7.71 (m, 1H).

Workup

  1. concentrationThe solution was concentrate
  2. customthe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-e83c18e1c3c44753b1d2945ef8963503
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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