Tetrahydrofuran → HCID 178445731, 화합물

HRID 1036390

반응식

HRID 1036390 반응식
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C@:12]1([CH3:18])[CH2:16][O:15][C:14](=[O:17])[NH:13]1)[CH:6]=[CH:5]2.O1CCCC1.[C:24]([C@@H:28]1[CH2:33][CH2:32][C@H:31](O)[CH2:30][CH2:29]1)([CH3:27])([CH3:26])[CH3:25].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>>[C:24]([C@H:28]1[CH2:33][CH2:32][C@H:31]([O:1][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[CH:8]=[C:7]([C@:12]2([CH3:18])[CH2:16][O:15][C:14](=[O:17])[NH:13]2)[CH:6]=[CH:5]3)[CH2:30][CH2:29]1)([CH3:27])([CH3:26])[CH3:25]

참가 물질

6

반응물 5

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 51066623(R)-4-(6-hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-oneHCID 178445811HCID 178445811, 화합물

생성물 1

HCID 178445731HCID 178445731, 화합물수율 393.9%

실험 절차

(R)-4-(6-hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-one (Example 4, 0.0509 g, 0.000209 mol) was dissolved in tetrahydrofuran (3.00 mL, 0.0370 mol) in a capped 40 mL EPA vial equipped with a magnetic stir bar. Cis-4-tert-butylcyclohexanol (0.0392 g, 0.000251 mol) was added, followed by triphenylphosphine (0.0878 g, 0.000335 mol) and the reaction was heated to reflux. Diisopropyl azodicarboxylate (0.0659 mL, 0.000335 mol) was added and the reaction was heated at reflux overnight with stirring. TLC analysis showed that the reaction was complete. The mixture was concentrated under vacuum. The resulting product was purified by flash chromatography (0-30% EtOAc in methylene chloride) to give 0.3141 g of the title compound (66% yield).

후처리

  1. customvial equipped with a magnetic stir bar
  2. temperaturethe reaction was heated to reflux
  3. temperaturethe reaction was heated
  4. temperatureat reflux overnight
  5. concentrationThe mixture was concentrated under vacuum
  6. customThe resulting product was purified by flash chromatography (0-30% EtOAc in methylene chloride)

출처 및 근거

ORD 기록
ord-f4954f41dcab491fb35b3a24d6d6ce2e
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546359B2

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