Sodium Iodide → N-[3,5-bis(decyloxy)phenyl]-N-[2-oxo-2-(phenylmethoxy)ethyl]glycine phenylmethyl ester

HRID 1757777Notes

Reaction equation

HRID 1757777 reaction equation
[CH2:1]([O:11][C:12]1[CH:13]=[C:14]([NH2:29])[CH:15]=[C:16]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].Br[CH2:31][C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33].CN(C)[C:44]1[C:53]2[C:48](=[CH:49][CH:50]=[CH:51][C:52]=2N(C)C)C=CC=1.[I-].[Na+]>C(#N)C.CN(C=O)C>[C:36]1([CH2:35][O:34][C:32](=[O:33])[CH2:31][N:29]([C:14]2[CH:13]=[C:12]([O:11][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH:17]=[C:16]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:15]=2)[CH2:31][C:32](=[O:33])[O:34][CH2:44][C:53]2[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=2)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 62576Benzyl bromoacetateHCID 88675Proton spongeHCID 103412613,5-Bis(decyloxy)benzeneamine

Product 1

HCID 10032668N-[3,5-bis(decyloxy)phenyl]-N-[2-oxo-2-(phenylmethoxy)ethyl]glycine phenylmethyl esterYield 45.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 20.0 g (0.0493 mol) of 3,5-bis(decyloxy)benzenamine, 23.6 ml (0.148 mol) of benzyl bromoacetate, 26.4 g (0.123 mol) of 1,8-bis(dimethylamino)naphthalene and 2.1 g of sodium iodide in 300 ml acetonitrile and 65 ml of DMF was stirred at reflux for 48 hours. The reaction mixture was concentrated under reduced pressure and the residue was extracted with ethyl acetate. The extract was washed with 0.5N HCl, with saturated NaHCO3, dried and concentrated under reduced pressure to an oil. Purification by HPLC using 10% ethyl acetate-hexane gave 15.7 g(45% yield, mp 55°-57°) of N-[3,5-bis(decyloxy)phenyl]-N-[2-oxo-2-(phenylmethoxy)ethyl]glycine phenylmethyl ester.

Workup

  1. temperatureat reflux for 48 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. extractionthe residue was extracted with ethyl acetate
  4. washThe extract was washed with 0.5N HCl, with saturated NaHCO3
  5. customdried
  6. concentrationconcentrated under reduced pressure to an oil
  7. customPurification by HPLC

Sources & evidence

ORD record
ord-281f6b347d424c1790ad2222892a2e35
Source dataset
uspto-grants-1995_08
Patent number
US05446189

Reaction notes

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