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Ammonium Chloride → 3-[2(S)-Ethyl-3-(4-propyloxymethyl-naphth-2-yl)-propionyl]-4(R)-benzyl-oxazolidin-2-one

HRID 264889
ノート
印刷プレビュー

反応式

HRID 264889 の反応式
[C:1]([N:6]1[C@H:10]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:9][O:8][C:7]1=[O:18])(=[O:5])[CH2:2][CH2:3][CH3:4].C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[CH2:29]([O:32][CH2:33][C:34]1[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:37]=[C:36]([CH2:44]Br)[CH:35]=1)[CH2:30][CH3:31].[Cl-].[NH4+]>O1CCCC1>[CH2:3]([C@@H:2]([CH2:44][C:36]1[CH:35]=[C:34]([CH2:33][O:32][CH2:29][CH2:30][CH3:31])[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:37]=1)[C:1]([N:6]1[C@H:10]([CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:9][O:8][C:7]1=[O:18])=[O:5])[CH3:4]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 2733832Lithium hexamethyldisilazaneHCID 11736739(4R)-4-benzyl-3-butanoyl-1,3-oxazolidin-2-oneHCID 214587034-Propoxymethyl-2-bromomethylnaphthalene

生成物 1

HCID 228657673-[2(S)-Ethyl-3-(4-propyloxymethyl-naphth-2-yl)-propionyl]-4(R)-benzyl-oxazolidin-2-one

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒
3 回

反応条件

温度
-75 °C

実験手順

30 ml of tetrahydrofuran and a solution of 2.97 g of 3-butyroyl-4(R)-benzyl-oxazolidin-2-one in 15 ml of tetrahydrofuran are added dropwise in succession to a solution, stirred at -75° C., of 12 ml of 1M lithium hexamethyldisilazide solution. The reaction mixture is stirred for 1 hour at -75° C., a solution of 3.52 g of 4-propoxymethyl-2-bromomethyl-naphthalene in 15 ml of tetrahydrofuran is added dropwise thereto and the mixture is then stirred further for 1 hour at -30° C. and for 3 hours at 0° C. After the dropwise addition at 0° C. of 2.7 ml of saturated ammonium chloride solution, the reaction mixture is concentrated by evaporation and the residue is partitioned between diethyl ether and water. The organic extracts are concentrated by evaporation and the residue is purified by FC (1 kg of silica gel, eluant: dichloromethane/hexane=3:1), yielding the title compound: Rf (dichloromethane/hexane=3:1)=0.24; FAB-MS (M+Na)+ =482.

後処理

  1. stirringthe mixture is then stirred further for 1 hour at -30° C. and for 3 hours at 0° C
  2. concentrationthe reaction mixture is concentrated by evaporation
  3. customthe residue is partitioned between diethyl ether and water
  4. concentrationThe organic extracts are concentrated by evaporation
  5. customthe residue is purified by FC (1 kg of silica gel, eluant: dichloromethane/hexane=3:1)

出典と根拠

ORDレコード
ord-4909a452e937443aa8ecf5191cfb1302
出典データセット
uspto-grants-1997_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05646143

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート