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Ammonium Chloride → (5R)-3-[4-(2-Benzyloxy-4-ethyl-phenoxy)-3-fluoro-phenyl]-5-hydroxymethyl-oxazolidin-2-one

HRID 626045
ノート
印刷プレビュー

反応式

HRID 626045 の反応式
C([O:8][C:9](=[O:35])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH3:25])=[CH:20][C:19]=2[O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[C:13]([F:34])[CH:12]=1)C1C=CC=CC=1.C([Li])CCC.[C:41](OC[C@@H]1OC1)(=[O:45])[CH2:42][CH2:43]C.[NH4+].[Cl-]>C1COCC1>[CH2:27]([O:26][C:19]1[CH:20]=[C:21]([CH2:24][CH3:25])[CH:22]=[CH:23][C:18]=1[O:17][C:14]1[CH:15]=[CH:16][C:11]([N:10]2[CH2:43][C@H:42]([CH2:41][OH:45])[O:8][C:9]2=[O:35])=[CH:12][C:13]=1[F:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1
参加物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 2724536(2R)-Oxiran-2-ylmethyl butanoateHCID 59191307[4-(2-Benzyloxy-4-ethyl-phenoxy)-3-fluoro-phenyl]-carbamic acid benzyl esterHCID 178418339Butyllithium

生成物 1

HCID 59191330(5R)-3-[4-(2-Benzyloxy-4-ethyl-phenoxy)-3-fluoro-phenyl]-5-hydroxymethyl-oxazolidin-2-one収率 52%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of [4-(2-Benzyloxy-4-ethyl-phenoxy)-3-fluoro-phenyl]-carbamic acid benzyl ester (0.31 mmol; 145 mg), under argon, in dry THF cooled to −78° C., was added n-Butyl lithium 2.3M in THF (0.46 mmol; 200 μL). the reaction mixture was stirred ten minutes and (R)-glycidyl butyrate (0.34 mmol; 48 μL) was added. The reaction was stirred overnight with slow warming to room temperature. The mixture was treated with saturated NH4Cl and extracted with ethyl acetate. Combined organic phases were dried over Na2SO4 and concentrated in vacuo. The title compound (70 mg; 52%) was obtained as . . . after purification by preparative TLC (eluant: dichloromethane/methanol: 95/5).

後処理

  1. stirringThe reaction was stirred overnight
  2. extractionextracted with ethyl acetate
  3. dry with materialCombined organic phases were dried over Na2SO4
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-a908948f8e724cf5a8a37a4ed31dd18d
出典データセット
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09309179B2

反応ノート

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