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

HRID 1110324Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1110324
[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]

Komponenten

8

Edukt 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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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°

Quellen und Nachweise

ORD-Eintrag
ord-c50c4b700a854171a4a9b972b628e874
Quelldatensatz
uspto-grants-1994_06
Patentnummer
US05324747

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