Sodium Sulfate → HCID 86701262、化合物

HRID 2276063ノート

反応式

HRID 2276063 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

HCID 86701262HCID 86701262、化合物収率 71%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
22 °C

実験手順

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]+).

後処理

  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)

出典と根拠

ORDレコード
ord-cd8940b0ccb3437a9b35c63b791030b5
出典データセット
uspto-grants-2015_09
特許番号
US09131690B2

反応ノート

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