Sodium Iodide → N-[3-(methoxycarbonyl)-5-(octadecyloxy)phenyl]-N-[2-(phenylmethoxy)-2-oxoethyl]glycine phenylmethyl ester

HRID 1110259Notes

Reaction equation

HRID 1110259 reaction equation
[CH3:1][O:2][C:3](=[O:30])[C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:7]=[C:6]([NH2:29])[CH:5]=1.Br[CH2:32][C:33]([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:34].CN(C)[C:45]1[C:54]2[C:49](=[CH:50][CH:51]=[CH:52][C:53]=2N(C)C)C=CC=1.[I-].[Na+]>CN(C=O)C>[C:37]1([CH2:36][O:35][C:33](=[O:34])[CH2:32][N:29]([C:6]2[CH:7]=[C:8]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:9]=[C:4]([C:3]([O:2][CH3:1])=[O:30])[CH:5]=2)[CH2:4][C:3](=[O:2])[O:30][CH2:45][C:54]2[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=2)[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 62576Benzyl bromoacetateHCID 88675Proton spongeHCID 193890883-Amino-5-(octadecyloxy)benzoic acid methyl ester

Product 1

HCID 19388997N-[3-(methoxycarbonyl)-5-(octadecyloxy)phenyl]-N-[2-(phenylmethoxy)-2-oxoethyl]glycine phenylmethyl esterYield 93.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3.25 g (7.74 mmol) of 3-amino-5-(octadecyloxy)benzoic acid methyl ester, 3.7 ml (23 mmol) of benzyl bromoacetate, 4.2 g (19.4 mmol) of 1,8-bis(dimethylamino)naphthalene and 0.3 g (2.2 mmol) of sodium iodide in 65 ml of acetronitrile and 20 ml of DMF was stirred and heated at reflux under argon for 48 hours. The reaction mixture was concentrated at reduced pressure and ethyl acetate was added to the residue. The extract was washed with 0.05N HCl, with saturated NaHCO3 solution, dried and concentrated at reduced pressure to a solid which was purified by HPLC using 15% ethyl acetate-hexane to give 2.6 g (48% yield, mp 62°-63°) of N-[3-(methoxycarbonyl)-5-(octadecyloxy)phenyl]-N-[2-oxo-2-(phenylmethoxy)ethyl]glycine phenylmethyl ester.

Workup

  1. temperatureheated
  2. temperatureat reflux under argon for 48 hours
  3. concentrationThe reaction mixture was concentrated at reduced pressure and ethyl acetate
  4. additionwas added to the residue
  5. washThe extract was washed with 0.05N HCl, with saturated NaHCO3 solution
  6. customdried
  7. concentrationconcentrated at reduced pressure to a solid which
  8. customwas purified by HPLC

Sources & evidence

ORD record
ord-ce6c00349472469a99a7e68b6a0d733b
Source dataset
uspto-grants-1994_06
Patent number
US05324747

Reaction notes

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