Sodium Iodide → HCID 19388920, compound

HRID 1757835Notes

Reaction equation

HRID 1757835 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+]>C(#N)C.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

7

Reactant 4

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

Product 1

HCID 19388920HCID 19388920, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

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 acetonitrile 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-616d6a93dc544c738882dcbc75bb91c5
Source dataset
uspto-grants-1995_08
Patent number
US05446189

Reaction notes

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