Triethylamine → 3-[5-(2-Methyl-[1,3]dioxolan-2-yl)-pentanoyl]-oxazolidin-2-one

HRID 322070노트

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HRID 322070 반응식
CCN([CH2:6][CH3:7])CC.[C:8](Cl)(=[O:13])[C:9](C)(C)[CH3:10].[O:15]1[CH2:19][CH2:18][NH:17][C:16]1=[O:20].[Li]CCCC.[Li].[C:27]([O:30][CH2:31][CH3:32])(=[O:29])[CH3:28]>C1COCC1>[CH3:28][C:27]1([CH2:6][CH2:7][CH2:10][CH2:9][C:8]([N:17]2[CH2:18][CH2:19][O:15][C:16]2=[O:20])=[O:13])[O:29][CH2:32][CH2:31][O:30]1

참가 물질

8

반응물 6

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 62493Pivaloyl chlorideHCID 739492-OxazolidinoneHCID 3028194LithiumHCID 178418339Butyllithium

생성물 1

HCID 154537573-[5-(2-Methyl-[1,3]dioxolan-2-yl)-pentanoyl]-oxazolidin-2-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

To a stirred solution of 2-2 (16.0 g, 85.5 mmol), NEt3 (13.1 ml, 94.1 mmol) and THF (400 mL) at −78° C. was added pivaloyl chloride (11.6 ml, 94.1 mmol). The mixture was warmed to 0° C. for 1.0 h and then recooled to −78° C. To a stirred solution of 2-oxazolidinone (9.3 g, 106.9 mmol) and THF (200 ml) at −78° C. was added nBuLi (43.0 ml, 106.9 mmol, 2.5M in hexanes) dropwise over 10 minutes. After 20 minutes, the lithium reagent was transferred to the mixed anhydride via cannula. After 10 minutes, the reaction was warmed to 0° C. for 1.0 h. The mixture was diluted with ethyl acetate, washed with sat. NaHCO3, brine, and dried over MgSO4. Following evaporative removal of the solvent, the residue was chromatographed (silica gel, 40%-50% EtOAc/hexanes) to give 2-3 as a colorless foam.

후처리

  1. customrecooled to −78° C
  2. waitAfter 10 minutes
  3. temperaturethe reaction was warmed to 0° C. for 1.0 h
  4. washwashed with sat. NaHCO3, brine
  5. dry with materialdried over MgSO4
  6. customremoval of the solvent
  7. customthe residue was chromatographed (silica gel, 40%-50% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-ba4689a5c6be4bc5ad66c4444783f98b
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06211191B1

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