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

HRID 19194노트

반응식

HRID 19194 반응식
[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]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 86635235Toluene-4-sulfonyloxymethyl-oxazolidine-3-carboxylic acid t-butyl esterHCID 178526745HCID 178526745, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
60 °C

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-35d5750b182c46519ed7608834d5ac46
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741327B2

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