Diisopropylethylamine → Acetic acid 4-[(5-isopropyl-[1,3,4]thiadiazol-2-yl)-(2-trimethylsilanyl-ethoxymethyl)-sulfamoyl]-phenyl ester

HRID 604459ノート

反応式

HRID 604459 の反応式
[CH:1]([C:4]1[S:8][C:7]([NH:9][S:10]([C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20](=[O:22])[CH3:21])=[CH:15][CH:14]=2)(=[O:12])=[O:11])=[N:6][N:5]=1)([CH3:3])[CH3:2].C(N(CC)C(C)C)(C)C.[CH3:32][Si:33]([CH3:40])([CH3:39])[CH2:34][CH2:35][O:36][CH2:37]Cl>ClCCl.CN(C)C1C=CN=CC=1>[CH:1]([C:4]1[S:8][C:7]([N:9]([CH2:37][O:36][CH2:35][CH2:34][Si:33]([CH3:40])([CH3:39])[CH3:32])[S:10]([C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20](=[O:22])[CH3:21])=[CH:15][CH:14]=2)(=[O:11])=[O:12])=[N:6][N:5]=1)([CH3:3])[CH3:2]

参加物

6

反応物 3

HCID 81531DiisopropylethylamineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 57543180Acetic acid 4-(5-isopropyl-[1,3,4]thiadiazol-2-ylsulfamoyl)-phenyl ester

生成物 1

HCID 57543195Acetic acid 4-[(5-isopropyl-[1,3,4]thiadiazol-2-yl)-(2-trimethylsilanyl-ethoxymethyl)-sulfamoyl]-phenyl ester収率 59.2%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

3.3 g Acetic acid 4-(5-isopropyl-[1,3,4]thiadiazol-2-ylsulfamoyl)-phenyl ester were dissolved in 12 ml dichloromethane. 2.69 ml N,N-diisopropylethylamine, 78 mg 4-dimethylaminopyridine and 2.1 g 2-(trimethylsilyl)ethoxymethyl chloride were added. The reaction mixture was stirred at room temperature for one hour. The solvent was removed in vacuo and the residue purified by flash chromatography on silica gel with the eluents n-heptane:ethyl acetate=1:1=>1:3 to obtain 2.7 g acetic acid 4-[(5-isopropyl-[1,3,4]thiadiazol-2-yl)-(2-trimethylsilanyl-ethoxymethyl)-sulfamoyl]-phenyl ester.

後処理

  1. customThe solvent was removed in vacuo
  2. customthe residue purified by flash chromatography on silica gel with the eluents n-heptane

出典と根拠

ORDレコード
ord-89c77b4874e346909e63c8197d0f79e7
出典データセット
uspto-grants-2011_03
特許番号
US07910612B2

反応ノート

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