Sodium Iodide → HCID 19388920, compound

HRID 1110279Notes

Reaction equation

HRID 1110279 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([NH2:30])[CH:8]=[C:9]([O: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][CH2:28][CH3:29])[CH:10]=1)(=[O:3])[CH3:2].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>[CH2:36]([O:35][C:33](=[O:34])[CH2:32][N:30]([C:7]1[CH:8]=[C:9]([O: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][CH2:28][CH3:29])[CH:10]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[CH:6]=1)[CH2:32][C:33](=[O:34])[O:35][CH2:45][C:54]1[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 62576Benzyl bromoacetateHCID 88675Proton spongeHCID 19389071HCID 19389071, compound

Product 1

HCID 19388920HCID 19388920, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.1 g (2.63 mmol) of 3-(acetylamino)-5-(octadecyloxy)benzenamine, 4.2 ml (26 mmol) of benzyl bromoacetate, 1.4 g (6.6 mmol) of 1,8-bis(dimethylamino)naphthalene and 0.4 g (2.63 mmol) of sodium iodide in 40 ml of acetronitrile and 5 ml of DMF was stirred at reflux for 48 hours. The solvents were removed at reduced pressure and the residue was purified by HPLC using 35% ethyl acetate-hexane to give 0.3 g (16% yield, mp 89°-90°) of N-[3-(acetylamino)-5-(octadecyloxy)phenyl]-N-[2-oxo-2-(phenylmethoxy)ethyl]glycine benzyl ester. The structure was confirmed by nmr and mass spectra.

Workup

  1. temperatureat reflux for 48 hours
  2. customThe solvents were removed at reduced pressure
  3. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-be1801f7fa6f45669f9e2c9c68f0ebe4
Source dataset
uspto-grants-1994_06
Patent number
US05324747

Reaction notes

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