Potassium Carbonate → (R*,S*)-(+/-)-5-(2-(5-(3-chlorophenyl)-2-oxo-3-oxazolidinyl)propyl)-1,3-benzodioxole-2,2-dicarboxylic acid, diethyl ester

HRID 5577

反応式

HRID 5577 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]2[O:12][C:11](=[O:13])[N:10]([C@@H:14]([CH3:24])[CH2:15][C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([OH:23])[CH:17]=3)[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.Br[C:26](Br)([C:32]([O:34][CH2:35][CH3:36])=[O:33])[C:27]([O:29][CH2:30][CH3:31])=[O:28].C(=O)([O-])[O-].[K+].[K+]>BrC(Br)(C(OCC)=O)C(OCC)=O.CC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]2[O:12][C:11](=[O:13])[N:10]([C@H:14]([CH3:24])[CH2:15][C:16]3[CH:21]=[CH:20][C:19]4[O:22][C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])([C:32]([O:34][CH2:35][CH3:36])=[O:33])[O:23][C:18]=4[CH:17]=3)[CH2:9]2)[CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 69427Propanedioic acid, 2,2-dibromo-, 1,3-diethyl esterHCID 67823889(R*,S*)-(+/-)-5-(3-chlorophenyl)-3-(2-(3,4-dihydroxyphenyl)-1-methylethyl)-2-oxazolidinone

生成物 1

HCID 15669208(R*,S*)-(+/-)-5-(2-(5-(3-chlorophenyl)-2-oxo-3-oxazolidinyl)propyl)-1,3-benzodioxole-2,2-dicarboxylic acid, diethyl ester収率 66.1%

試薬・触媒・溶媒 2

HCID 69427Propanedioic acid, 2,2-dibromo-, 1,3-diethyl ester触媒HCID 180Acetone溶媒

実験手順

A mixture of 0.8 g of the above oxazolidinone, 0.74 g of diethyl dibromomalonate, 1.2 g of anhydrous potassium carbonate and 20 ml of acetone are stirred overnight with the addition of a few drops of diethyl dibromomalonate. The mixture is filtered, washed with acetone and the combined filtrate and wash are evaporated to a yellow oil. The oil is purified by flash chromatography, eluting with 5 percent acetone in toluene. The pure fractions are combined and evaporated, giving 766 mg of (R*,S*)-(±)-5-(2-(5-(3-chlorophenyl)-2-oxo-3-oxazolidinyl)propyl)-1,3-benzodioxole-2,2-dicarboxylic acid, diethyl ester as a colorless oil.

後処理

  1. filtrationThe mixture is filtered
  2. washwashed with acetone
  3. washthe combined filtrate and wash
  4. customare evaporated to a yellow oil
  5. customThe oil is purified by flash chromatography
  6. washeluting with 5 percent acetone in toluene
  7. customevaporated

出典と根拠

ORDレコード
ord-463370cd2f4149d4a74c16289bb0ce5f
出典データセット
uspto-grants-1993_09
特許番号
US05245053

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