Methyl iodide → Methyl corosolate

HRID 1367637노트

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HRID 1367637 반응식
[CH3:1][C@H:2]1[C@H:29]([CH3:30])[C@@H:28]2[C@@:5]([C:32]([OH:34])=[O:33])([CH2:6][CH2:7][C@@:8]3([CH3:31])[C@:13]4([CH3:27])[CH2:14][CH2:15][C@H:16]5[C:21]([CH3:23])([CH3:22])[C@@H:20]([OH:24])[C@H:19]([OH:25])[CH2:18][C@:17]5([CH3:26])[C@H:12]4[CH2:11][CH:10]=[C:9]32)[CH2:4][CH2:3]1.IC.[C:37](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][C@H:2]1[C@H:29]([CH3:30])[C@@H:28]2[C@@:5]([C:32]([O:34][CH3:37])=[O:33])([CH2:6][CH2:7][C@@:8]3([CH3:31])[C@:13]4([CH3:27])[CH2:14][CH2:15][C@H:16]5[C:21]([CH3:23])([CH3:22])[C@@H:20]([OH:24])[C@H:19]([OH:25])[CH2:18][C@:17]5([CH3:26])[C@H:12]4[CH2:11][CH:10]=[C:9]32)[CH2:4][CH2:3]1

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 6918774Corosolic acid

생성물 1

HCID 14109751Methyl corosolate수율 83%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

A mixture of corosolic acid (2.0 g, 4.34 mmol), iodomethane (1 mL, 16 mmol), potassium carbonate (4.5 g, 32.6 mmol) and acetone (60 mL) was stirred at rt for 16 h. After completion of the reaction, the solids were filtered off and the solvent was evaporated under reduced pressure. The residue was chromatographed over silica gel column using chloroform-methanol (10%) as eluent to furnish methyl corosolate (1.7 g, 83%), which was recrystallised from chloroform-hexane, m.p. 208-210° C.; IR (KBr): 3432, 2946, 2872, 1728, 1455, 1230, 1197, 1049 cm−1; 1H NMR (400 MHz, CDCl3) δ 0.75 (3H, s, CH3), 0.83 (3H, s, CH3), 0.85 (3H, d, J=6.5 Hz, CH3), 0.94 (3H, d, J=5.7 Hz, CH3), 0.99 (3H, s, CH3), 1.03 (3H, s, CH3), 1.08 (3H, s, CH3), 2.23 (1H, d, J=11.0 Hz, H-18), 3.0 (1H, d, J=8.4 Hz, H-3), 3.60 (3H, s, —COOCH3), 3.62-3.71 (1H, m, H-2), 5.25 (1H, t, J=3.4 Hz, H-12); LCMS (negative ion mode): m/z 485 (M−H)−.

후처리

  1. customAfter completion of the reaction
  2. filtrationthe solids were filtered off
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was chromatographed over silica gel column

출처 및 근거

ORD 기록
ord-f911532d017e4c1ba7e594675be67879
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07893263B2

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