Dimethylformamide → (R)-2,2-dimethyl-4-(3-nitro-pyrazol-1-ylmethyl)-oxazolidine-3-carboxylic acid t-butyl ester

HRID 19194ノート

反応式

HRID 19194 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][O:10][CH:9]1[CH2:13]OS(C1C=CC(C)=CC=1)(=O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:25](=O)([O-])[O-].[K+].[K+].[N+:31]([C:34]1[CH:38]=CN[N:35]=1)([O-:33])=[O:32].[CH3:39][N:40]([CH3:43])C=O>C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[C@H:12]([CH2:39][N:40]2[CH:43]=[CH:38][C:34]([N+:31]([O-:33])=[O:32])=[N:35]2)[CH2:11][O:10][C:9]1([CH3:13])[CH3:25])=[O:7])([CH3:2])([CH3:3])[CH3:4]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 86635235Toluene-4-sulfonyloxymethyl-oxazolidine-3-carboxylic acid t-butyl esterHCID 178526745HCID 178526745、化合物

生成物 1

HCID 57920020(R)-2,2-dimethyl-4-(3-nitro-pyrazol-1-ylmethyl)-oxazolidine-3-carboxylic acid t-butyl ester収率 65%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

To a stirred mixture of (S)-2,2-dimethyl-4-(toluene-4-sulfonyloxymethyl-oxazolidine-3-carboxylic acid t-butyl ester (2.20 g, 5.71 mmol) in N,N-dimethylformamide (10 mL) was added potassium carbonate (0.93 g, 6.73 mmol) and 3-nitro-1H-pyrazole (prepared as in Example 5, 0.59 mg, 5.20 mmol). After addition was complete the mixture was stirred at 60° C. for 18 h. The reaction mixture was diluted with ethyl acetate, washed with water followed by a saturated sodium chloride solution and dried over magnesium sulfate. The organic layer was concentrated, and the crude product was purified by ISCO flash chromatography (Teledyne Isco RediSep Flash Column 40 g; 0% to 100% ethyl acetate/hexanes) to afford (R)-2,2-dimethyl-4-(3-nitro-pyrazol-1-ylmethyl)-oxazolidine-3-carboxylic acid t-butyl ester (1.21 g, 65%) as a colorless oil: LR-ES-MS m/z calculated for C14H22N4O5 [M]+ 326, observed 327 [M+H]+.

後処理

  1. additionAfter addition
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationThe organic layer was concentrated
  5. customthe crude product was purified by ISCO flash chromatography (Teledyne Isco RediSep Flash Column 40 g; 0% to 100% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-35d5750b182c46519ed7608834d5ac46
出典データセット
uspto-grants-2010_06
特許番号
US07741327B2

反応ノート

読み込み中…