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

HRID 1108383노트

반응식

HRID 1108383 반응식
[CH3:1][C:2]1([CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=O)[O:6][CH2:5][CH2:4][O:3]1.CCN(CC)CC.C(Cl)(=O)C(C)(C)C.[O:28]1[CH2:32][CH2:31][NH:30][C:29]1=[O:33].[Li]CCCC.[Li]>C(OCC)(=O)C.C1COCC1>[CH3:1][C:2]1([CH2:7][CH2:8][CH2:9][CH2:10][C:11]([N:30]2[CH2:31][CH2:32][O:28][C:29]2=[O:33])=[O:13])[O:3][CH2:4][CH2:5][O:6]1

참가 물질

9

반응물 6

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 739492-OxazolidinoneHCID 3028194LithiumHCID 154537565-(2-Methyl-[1,3]dioxolan-2-yl)-pentanoic acidHCID 178418339Butyllithium

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

반응 조건

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-ad1f49ab6fdd4a439bd55135a800d4a2
출처 데이터셋
uspto-grants-2000_05
특허 번호
US06066648

반응 노트

불러오는 중…