Sodium Iodide → N-[3-[2-[2-(2-Ethoxyethoxy)ethoxy]ethoxy]-5-[(12-phenoxydodecyl)oxy]phenyl]-N-(2-methoxy-2-oxoethyl)glycine methyl ester

HRID 1110324Notes

Reaction equation

HRID 1110324 reaction equation
[CH3:1][O:2][C:3](=[O:38])[CH2:4][N:5]([C:11]1[CH:16]=[C:15]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][O:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:14]=[C:13]([OH:37])[CH:12]=1)[CH2:6][C:7]([O:9][CH3:10])=[O:8].[CH2:39]([O:41][CH2:42][CH2:43][O:44][CH2:45][CH2:46][O:47][CH2:48][CH2:49]Br)[CH3:40].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].COC(=O)CN(C1C=CC(OCCCCCCCCCCCCOC2C=CC=CC=2)=C(OCCOCCOCCOCC)C=1)CC(OC)=O>CC(C)=O.CN(C=O)C>[CH3:1][O:2][C:3](=[O:38])[CH2:4][N:5]([C:11]1[CH:16]=[C:15]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][O:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:14]=[C:13]([O:37][CH2:49][CH2:48][O:47][CH2:46][CH2:45][O:44][CH2:43][CH2:42][O:41][CH2:39][CH3:40])[CH:12]=1)[CH2:6][C:7]([O:9][CH3:10])=[O:8]

Participants

8

Reactant 5

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 147041761-Bromo-2-(2-(2-ethoxyethoxy)ethoxy)ethaneHCID 19018973N-[3-[2-[2-(2-ethoxyethoxy)ethoxy]ethoxy]-4-[(12-phenoxydodecyl)oxy]phenyl]-N-(2-methoxy-2-oxoethyl)glycine methyl esterHCID 19388995N-[3-hydroxy-5-[(12-phenoxydodecyl)oxy]phenyl]-N-(2-methoxy-2-oxoethyl)glycine methyl ester

Product 1

HCID 54392152N-[3-[2-[2-(2-Ethoxyethoxy)ethoxy]ethoxy]-5-[(12-phenoxydodecyl)oxy]phenyl]-N-(2-methoxy-2-oxoethyl)glycine methyl esterYield 74%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.2 g (2.27 mmol) of N-[3-hydroxy-5[(12-phenoxydodecyl)oxy]phenyl]-N-(2-methoxy-2-oxoethyl)glycine methyl ester, 2.73 g (11.37 mmol) of 2-[2-(2-ethoxyethoxy)ethoxy]ethyl bromide, 0.94 g (6.8 mmol) of potassium carbonate and 1.0 g (6.8 mmol) of sodium iodide in 40 ml of acetone and 20 ml of DMF was stirred at reflux under argon for 64 hours. After the usual workup the product was purified by HPLC using 40% ethyl acetate-hexane to give 1.16 g (74% yield), mp<24°, of N-[3-[2-[2-(2-ethoxyethoxy)ethoxy]ethoxy]-4-[(12-phenoxydodecyl)oxy]phenyl]-N-(2-methoxy-2-oxoethyl)glycine methyl ester.

Workup

  1. temperatureat reflux under argon for 64 hours
  2. customAfter the usual workup the product was purified by HPLC
  3. customto give 1.16 g (74% yield), mp<24°

Sources & evidence

ORD record
ord-c50c4b700a854171a4a9b972b628e874
Source dataset
uspto-grants-1994_06
Patent number
US05324747

Reaction notes

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