Ethyl bromoacetate → HCID 59364365, compound

HRID 426040Notes

Reaction equation

HRID 426040 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([CH3:23])=[C:8]([CH:10]([OH:22])[CH2:11][CH2:12][N:13]([CH3:21])[C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH:9]=1.Br[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27].[NH4+].[Cl-]>C1COCC1.C1COCC1.CN(C=O)C>[C:16]([O:15][C:14]([N:13]([CH3:21])[CH2:12][CH2:11][CH:10]([C:8]1[CH:9]=[C:4]([Cl:3])[CH:5]=[CH:6][C:7]=1[CH3:23])[O:22][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[O:20])([CH3:19])([CH3:17])[CH3:18]

Participants

7

Reactant 4

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 59364372HCID 59364372, compound

Product 1

HCID 59364365HCID 59364365, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

To a suspension of NaH (0.5 g, 12.5 mmol) in THF (400 mL) at 0-5° C. was added drop wise a solution of tert-butyl 3-(5-chloro-2-methylphenyl)-3-hydroxypropyl(methyl)carbamate (1.3 g, 4.15 mmol) in anhydrous THF/DMF (24/16 mL), the reaction mixture was stirred for 1 h at room temperature. A solution of ethyl bromoacetate (2.1 g, 12.5 mmol) in anhydrous THF (13 mL) was added drop wise to the above mixture, the reaction mixture was stirred at room temperature overnight. The reaction mixture was poured into saturated aqueous NH4Cl, and then extracted with ethyl acetate. The organic layer was washed with water and brine, dried over Na2SO4, filtered and concentrated in vacuo to afford crude ethyl 2-(3-(tert-butoxycarbonyl(methyl)amino)-1-(5-chloro-2-methylphenyl)propoxy)acetate (800 mg, 60%), which was used for next step without purification. 1H NMR (CDCl3, 400 MHz) δ 1.45 (s, 9H), 1.68 (s, 3H), 1.87 (m, 2H), 2.25 (m, 2H), 2.90 (s, 3H), 4.63 (m, 1H), 7.13 (m, 2H), 7.38 (m, 1H).

Workup

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2db8141fd3b24f4f8ce3545b721e9e50
Source dataset
uspto-grants-2012_01
Patent number
US08106221B2

Reaction notes

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