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

HRID 1110324ノート

反応式

HRID 1110324 の反応式
[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]

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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°

出典と根拠

ORDレコード
ord-c50c4b700a854171a4a9b972b628e874
出典データセット
uspto-grants-1994_06
特許番号
US05324747

反応ノート

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