Sodium Sulfate → HCID 86701262, 화합물

HRID 2276063노트

반응식

HRID 2276063 반응식
[C:1]([O:6][C@@H:7]1[C@@H:15]([CH2:16][CH2:17][OH:18])[C:14](=[O:19])[O:13][CH2:12][C@H:11]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:10](=[O:28])[O:9][C@H:8]1[CH3:29])(=[O:5])[CH:2]([CH3:4])[CH3:3].[CH3:30]N(C1C2C(N(C)C)=CC=CC=2C=CC=1)C.[O-]S([O-])(=O)=O.[Na+].[Na+].F[B-](F)(F)F.C[O+](C)C>C(Cl)Cl.CCOC(C)=O>[C:1]([O:6][C@@H:7]1[C@@H:15]([CH2:16][CH2:17][O:18][CH3:30])[C:14](=[O:19])[O:13][CH2:12][C@H:11]([NH:20][C:21]([O:23][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:22])[C:10](=[O:28])[O:9][C@H:8]1[CH3:29])(=[O:5])[CH:2]([CH3:4])[CH3:3]

참가 물질

7

반응물 4

HCID 24436Sodium SulfateHCID 88675Proton spongeHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 86701260HCID 86701260, 화합물

생성물 1

HCID 86701262HCID 86701262, 화합물수율 71%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

반응 조건

온도
22 °C

실험 절차

A round bottom flask was charged with (3S,6S,7R,8R)-3-(tert-butoxycarbonyl-amino)-8-(2-hydroxyethyl)-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl isobutyrate (200 mg, 0.48 mmol), Proton Sponge™ (700 mg, 4.05 mmol), Na2SO4 in CH2Cl2 (10 mL) at 0° C. To the resulting suspension was added trimethyloxonium tetrafluoroborate (Me3OBF4, 320 mg, 2.16 mmol), and the suspension was warmed to room temperature (about 22° C.) and stirred for 5 h. The mixture was diluted with EtOAc, filtered, and the filtrate was washed successively with water and 1M NaHSO4. The organics were dried over Na2SO4, filtered, and the filtrate was concentrated under reduced pressure. Purification of the crude product via column chromatography (hexanes/EtOAc gradient) afforded the title compound (140 mg, 71%) as a clear oil: 1H NMR (300 MHz, CDCl3) δ 5.41-5.16 (m, J=0.9 Hz, 2H), 5.06 (t, J=9.9 Hz, 1H), 4.94-4.73 (m, 2H), 3.69-3.52 (m, 1H), 3.42-3.27 (m, 2H), 3.26 (s, J=0.9 Hz, 3H), 2.80-2.67 (m, 1H), 2.60 (dt, J=13.9, 7.0 Hz, 1H), 2.08-1.86 (m, 1H), 1.66-1.55 (m, 1H), 1.45 (s, 9H), 1.27 (d, J=6.3 Hz, 3H), 1.20 (d, J=7.0 Hz, 6H); ESIMS m/z 454 ([M+Na]+).

후처리

  1. filtrationfiltered
  2. washthe filtrate was washed successively with water and 1M NaHSO4
  3. dry with materialThe organics were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customPurification of the crude product via column chromatography (hexanes/EtOAc gradient)

출처 및 근거

ORD 기록
ord-cd8940b0ccb3437a9b35c63b791030b5
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09131690B2

반응 노트

불러오는 중…