Sodium Chloride → (S)-3-Hept-6-enoyl-4-isopropyl-oxazolidin-2-one

HRID 1638186노트

반응식

HRID 1638186 반응식
[CH:1]([C@H:4]1[CH2:8][O:7][C:6](=[O:9])[NH:5]1)([CH3:3])[CH3:2].[Li]CCCC.[C:15](Cl)(=[O:22])[CH2:16][CH2:17][CH2:18][CH2:19][CH:20]=[CH2:21].[Na+].[Cl-]>C1COCC1.CCCCCC>[C:15]([N:5]1[C@@H:4]([CH:1]([CH3:3])[CH3:2])[CH2:8][O:7][C:6]1=[O:9])(=[O:22])[CH2:16][CH2:17][CH2:18][CH2:19][CH:20]=[CH2:21]

참가 물질

7

반응물 4

HCID 5234Sodium ChlorideHCID 7157133(4S)-4-(propan-2-yl)-1,3-oxazolidin-2-oneHCID 108556156-Heptenoyl chlorideHCID 178418339Butyllithium

생성물 1

HCID 11053746(S)-3-Hept-6-enoyl-4-isopropyl-oxazolidin-2-one수율 92%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

실험 절차

A solution of 2.08 g (16.10 mmol, 1 equivalent) of (4S)-4-isopropyl-oxazolidin-2-one in 15 ml of THF is cooled to -78° C. and mixed drop by drop with 11.6 ml (18.52 mmol, 1.15 equivalents) of a 1.6 M solution of n-BuLi solution in hexane. Then, a solution of 2.95 g (20.13 mmol, 1.25 equivalents) of hept-6-enoyl chloride in 10 ml of THF is added at -78° C. It is allowed to heat to room temperature, and the reaction solution is poured onto saturated NaCl solution. The aqueous phase is extracted with ether, the combined organic phases are dried on MgSO4, and the solvent is distilled off in a rotary evaporator. The residue is purified by column chromatography with PE:DE=3:1. 3.55 g (14.82 mmol, 92%) of oxazolidinone 21 is obtained as a colorless oil.

후처리

  1. extractionThe aqueous phase is extracted with ether
  2. customthe combined organic phases are dried on MgSO4
  3. distillationthe solvent is distilled off in a rotary evaporator
  4. customThe residue is purified by column chromatography with PE

출처 및 근거

ORD 기록
ord-7f2505819c1b4c848d276efcf12096f4
출처 데이터셋
uspto-grants-2000_03
특허 번호
US06043372

반응 노트

불러오는 중…