Diisopropylethylamine → (5R)-3-(3-Fluorophenyl)-5-[(4-methyl-1H-1,2,3-triazol-1-yl)methyl]-1,3-oxazolidin-2-one

HRID 747228ノート

反応式

HRID 747228 の反応式
C(N(CC)C(C)C)(C)C.[NH2:10][CH2:11][C@@H:12]1[O:16][C:15](=[O:17])[N:14]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=2)[CH2:13]1.Cl[CH:26](Cl)[C:27](=[N:29][NH:30]S(C1C=CC(C)=CC=1)(=O)=O)[CH3:28]>CO>[F:24][C:20]1[CH:19]=[C:18]([N:14]2[CH2:13][C@H:12]([CH2:11][N:10]3[CH:26]=[C:27]([CH3:28])[N:29]=[N:30]3)[O:16][C:15]2=[O:17])[CH:23]=[CH:22][CH:21]=1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 11401559(5S)-5-(aminomethyl)-3-(3-fluorophenyl)-1,3-oxazolidin-2-oneHCID 73181071N'-[2,2-dichloro-1-methylethylidene]-4-methylbenzenesulfonohydrazide

生成物 1

HCID 58778317(5R)-3-(3-Fluorophenyl)-5-[(4-methyl-1H-1,2,3-triazol-1-yl)methyl]-1,3-oxazolidin-2-one収率 70.2%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

N,N-Diisopropylethylamine (3.20 mL, 18.35 mM) was added to a solution of (5S)-5-(aminomethyl)-3-(3-fluorophenyl)-1,3-oxazolidin-2-one (0.77 g, 3.57 mM; see Dong Pharmaceuticals WO 0194342) in anhydrous methanol (25 mL). The solution was cooled to 0° C., and N′-[2,2-dichloro-1-methylethylidene]-4-methylbenzenesulfonohydrazide (1.28 g, 4.58 mM) was added. The solution was warmed to room temperature and stirred overnight. The reaction mixture was then concentrated under vacuum and chromatographed on silica gel using 2% methanol/dichloromethane to give 0.71 g of the title product.

後処理

  1. temperatureThe solution was warmed to room temperature
  2. concentrationThe reaction mixture was then concentrated under vacuum
  3. customchromatographed on silica gel using 2% methanol/dichloromethane

出典と根拠

ORDレコード
ord-06845fd9ba70447abe3ec36d64e84578
出典データセット
uspto-grants-2008_07
特許番号
US07396847B2

反応ノート

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