Diethyl Ether → benzyl[(2S)-1-{[tert-butyl(diphenyl)silyl]oxy}-5-fluoro-6-oxohexan-2-yl](3-methylbutyl)carbamate

HRID 1524349노트

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HRID 1524349 반응식
C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:11])(=O)=O)=CC=1.[CH2:21]([O:28][C:29](=[O:61])[N:30]([C@@H:36]([CH2:56][CH2:57][CH2:58][CH:59]=[O:60])[CH2:37][O:38][Si:39]([C:52]([CH3:55])([CH3:54])[CH3:53])([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH2:31][CH2:32][CH:33]([CH3:35])[CH3:34])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CCOCC>CC(O)C.C1COCC1>[CH2:21]([O:28][C:29](=[O:61])[N:30]([C@@H:36]([CH2:56][CH2:57][CH:58]([F:11])[CH:59]=[O:60])[CH2:37][O:38][Si:39]([C:52]([CH3:53])([CH3:54])[CH3:55])([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:46]1[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=1)[CH2:31][CH2:32][CH:33]([CH3:34])[CH3:35])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

참가 물질

5

반응물 3

HCID 3283Diethyl EtherHCID 588007N-FluorobenzenesulfonimideHCID 86708051benzyl[(2S)-1-{[tert-butyl(diphenyl)silyl]oxy}-6-oxohexan-2-yl](3-methylbutyl)carbamate

생성물 1

HCID 89916921benzyl[(2S)-1-{[tert-butyl(diphenyl)silyl]oxy}-5-fluoro-6-oxohexan-2-yl](3-methylbutyl)carbamate

시약·촉매·용매 1

HCID 22597222Tetrahydrofuran 2-propanol용매2회

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온도
-20 °C

실험 절차

Racemic 5-benzyl-2-2,3-trimethylimidazolidin-4-one dichloroacetic acid (109 mg, 0.314 mmol) and N-fluorobenzenesulfonimide (593 mg, 1.88 mmol) were dissolved in 10% i-PrOH-THF (3.75 mL). The reaction mixture was cooled to −20° C., and the compound from Step 7 (900 mg, 1.57 mmol) in 1.25 mL of 10% i-PrOH-THF was added. The reaction mixture was stirred at −20° C. for 24 hours, 2 volumes of ether were added, and the resulting mixture was vigorously stirred, filtered through Davisil® silica (W.R. Grace & Co.-Conn.), and eluted with ether. 5 mL of methyl sulfide was added to the eluted reaction mixture. The reaction mixture was partitioned between EtOAc and saturated aqueous NaHCO3 and extracted with EtOAc (2×). The combined organics were washed with brine, dried over MgSO4, filtered and concentrated in vacuo to afford the title compound which was used directly at Step 9. 1H NMR (DMSO-d6): δ7.66-7.52 (m, 5H), 7.51-7.25 (m, 10H), 5.08 (s, 2H), 4.90-4.83 (m, 1H), 3.70-3.55 (m, 1H), 3.53-3.36 (m, 2H), 3.17-2.99 (m, 2H), 1.63-1.32 (m, 7H), 0.96 (s, 9H), 0.88-0.72 (m 6H), aldehyde signal missing due to hydrate form.

후처리

  1. stirringthe resulting mixture was vigorously stirred
  2. filtrationfiltered through Davisil® silica (W.R. Grace & Co.-Conn.)
  3. washeluted with ether
  4. addition5 mL of methyl sulfide was added to the eluted reaction mixture
  5. customThe reaction mixture was partitioned between EtOAc and saturated aqueous NaHCO3
  6. extractionextracted with EtOAc (2×)
  7. washThe combined organics were washed with brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-2cd5724d397a4c03bac236b2269040ef
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09079834B2

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