1-Bromodecane → N-(2-methoxy-2-oxoethyl)-N-[3,5-bis(decyloxy) phenyl]glycine methyl ester

HRID 1110291Notes

Reaction equation

HRID 1110291 reaction equation
[CH3:1][O:2][C:3](=[O:19])[CH2:4][N:5]([C:11]1[CH:16]=[C:15]([OH:17])[CH:14]=[C:13]([OH:18])[CH:12]=1)[CH2:6][C:7]([O:9][CH3:10])=[O:8].Br[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][O:2][C:3](=[O:19])[CH2:4][N:5]([CH2:6][C:7]([O:9][CH3:10])=[O:8])[C:11]1[CH:16]=[C:15]([O:17][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:14]=[C:13]([O:18][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:12]=1

Participants

5

Reactant 3

HCID 81731-Bromodecane2×HCID 11430Potassium CarbonateHCID 19389065HCID 19389065, compound

Product 1

HCID 15232831N-(2-methoxy-2-oxoethyl)-N-[3,5-bis(decyloxy) phenyl]glycine methyl esterYield 52.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 0.50 g (1.86 mmol) of N-[(3,5-Dihydroxy)phenyl]-N-(2-methoxy-2-oxoethyl)glycine methyl ester, 0.81 ml (3.9 mmol) of 1-bromodecane and 0.77 g (5.57 mmol) of potassium carbonate in 15 ml of acetone was stirred at reflux for 24 hours. An additional 0.8 ml of 1-bromodecane was added and reflux was continued for 48 hours. The reaction mixture was filtered through a Celite pad and the filtrate was concentrated at reduced pressure to an oil which was purified by HPLC using 15% ethyl acetate-hexane to give 0.54 g (52% yield) of N-(2-methoxy-2-oxoethyl)-N-[3,5-bis-(decyloxy)phenyl]glycine methyl ester as an oil. The nmr and mass spectra of this product were identical to those obtained using the procedure of Example 5.

Workup

  1. temperatureat reflux for 24 hours
  2. temperaturereflux
  3. filtrationThe reaction mixture was filtered through a Celite pad
  4. concentrationthe filtrate was concentrated at reduced pressure to an oil which
  5. customwas purified by HPLC

Sources & evidence

ORD record
ord-73af0fc200664312b4b71f9c137f43f3
Source dataset
uspto-grants-1994_06
Patent number
US05324747

Reaction notes

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