Tetrahydrofuran → HCID 89827530, 화합물

HRID 525354노트

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HRID 525354 반응식
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:10]([O:12]C)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:20]1[CH2:24]OCC1.[CH2:25]([Mg]Br)[CH3:26].CCOC(C)=O>CCCCCC>[CH2:20]([C:10]([OH:12])([CH2:25][CH3:26])[C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:24]

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 10967413HCID 10967413, 화합물HCID 178418443HCID 178418443, 화합물

생성물 1

HCID 89827530HCID 89827530, 화합물수율 90%

시약·촉매·용매 1

HCID 8058Hexane용매

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온도
0 °C

실험 절차

To a two-necked 50 mL round bottom flask were added (R)-methyl 2-((tert-butoxycarbonyl)amino)-2-phenylacetate (1.2 g, 5.68 mmol) and dry THF (30 mL). The resulting mixture was cooled to 0° C. Ethyl magnesium bromide (3.02 g, 22.72 mmol) (3M solution in diethyl ether) was added dropwise, and the mixture was slowly allowed to warm to ambient temperature. The mixture was then stirred at ambient temperature for 24 hours. After completion of reaction (monitored by TLC, TLC eluent: 30% EtOAc in hexane), the mixture was quenched in NH4Cl solution and extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered, and concentrated to yield 1.2 g (90.0%) of (R)-tert-butyl (2-ethyl-2-hydroxy-1-phenylbutyl)carbamate as a white solid. 1H NMR (300 MHz, CDCl3) δ: 7.35-7.26 (m, 5H), 5.56 (d, J=9.1 Hz, 1H), 4.61 (d, J=9.4 Hz, 1H), 1.68-1.63 (m, 2H), 1.39 (s, 9H), 1.32-1.22 (m, 2H), 0.92 (t, J=7.4 Hz, 3H), 0.80 (t, J=7.4 Hz, 3H).

후처리

  1. temperatureto warm to ambient temperature
  2. customthe mixture was quenched in NH4Cl solution
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-21867e90f3524476bdb49cd01e3f4b5e
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340549B2

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