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

HRID 1110324노트

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[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]

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실험 절차

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.

후처리

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

출처 및 근거

ORD 기록: ord-c50c4b700a854171a4a9b972b628e874
출처 데이터셋: uspto-grants-1994_06
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US05324747

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