Water → (4R)-{2-[5-(5-Cyclohexylpent-1-ynyl)thiophen-2-yl]}ethyl-4-methyloxazolidin-2-one

HRID 1063440노트

반응식

HRID 1063440 반응식
Br[C:2]1[S:6][C:5]([CH2:7][CH2:8][N:9]2[C@H:13]([CH3:14])[CH2:12][O:11][C:10]2=[O:15])=[CH:4][CH:3]=1.[CH:16]1([CH2:22][CH2:23][CH2:24][C:25]#[CH:26])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.C(N(CC)CC)C.O>CN(C)C=O.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:16]1([CH2:22][CH2:23][CH2:24][C:25]#[C:26][C:2]2[S:6][C:5]([CH2:7][CH2:8][N:9]3[C@H:13]([CH3:14])[CH2:12][O:11][C:10]3=[O:15])=[CH:4][CH:3]=2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

참가 물질

8

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 15172912(Pent-4-yn-1-yl)cyclohexaneHCID 69338201(4R)-[2-(5-Bromothiophen-2-yl)]ethyl-4-methyloxazolidin-2-one

생성물 1

HCID 69338073(4R)-{2-[5-(5-Cyclohexylpent-1-ynyl)thiophen-2-yl]}ethyl-4-methyloxazolidin-2-one수율 82%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

(4R)-[2-(5-Bromothiophen-2-yl)]ethyl-4-methyloxazolidin-2-one (450 mg, 1.55 mmol) obtained in Example 1 (g) was dissolved in dimethylformamide (4.5 ml), and 5-cyclohexylpent-1-yne (50% xylene solution) (1.4 g, 4.65 mmol), triethylamine (2.16 ml, 15.5 mmol), copper (I) iodide (30 mg, 0.16 mmol) and dichlorobis(triphenylphosphine)palladium (109 mg, 0.16 mmol) were added thereto, and then the reaction mixture was stirred for 2 hours at 80° C. under a nitrogen atmosphere. The reaction solution was poured into water, extracted with ethyl acetate, and the ethyl acetate layer was washed with a saturated aqueous sodium chloride solution. After the ethyl acetate layer was dried over anhydrous sodium sulfate, the solvent was concentrated in vacuo, and the residue was purified by chromatography on a silica gel column (elution solvent; hexane:ethyl acetate=4:1-3:2) to afford the title compound (56 mg, 82% yield).

후처리

  1. extractionextracted with ethyl acetate
  2. washthe ethyl acetate layer was washed with a saturated aqueous sodium chloride solution
  3. dry with materialAfter the ethyl acetate layer was dried over anhydrous sodium sulfate
  4. concentrationthe solvent was concentrated in vacuo
  5. customthe residue was purified by chromatography on a silica gel column (elution solvent; hexane:ethyl acetate=4:1-3:2)

출처 및 근거

ORD 기록
ord-e427cc11050a4e17a0ad29916b6eb517
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06964976B2

반응 노트

불러오는 중…