Methyl iodide → 4-{2-(2-Ethoxycarbonyl-ethyl)-3-[6-(4'-methanesulfonyl-5-methoxymethyl-biphenyl-3-yloxy)-hexyl]-phenoxy}-butyric acid ethyl ester

HRID 416974노트

반응식

HRID 416974 반응식
[CH2:1]([O:3][C:4](=[O:47])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:23]=[C:24]([C:30]3[CH:35]=[CH:34][C:33]([S:36]([CH3:39])(=[O:38])=[O:37])=[CH:32][CH:31]=3)[CH:25]=[C:26]([CH2:28][OH:29])[CH:27]=2)[C:10]=1[CH2:40][CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH3:2].[H-].[Na+].I[CH3:51]>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:47])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:23]=[C:24]([C:30]3[CH:35]=[CH:34][C:33]([S:36]([CH3:39])(=[O:38])=[O:37])=[CH:32][CH:31]=3)[CH:25]=[C:26]([CH2:28][O:29][CH3:51])[CH:27]=2)[C:10]=1[CH2:40][CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH3:2]

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 594968084-{2-(2-Ethoxycarbonyl-ethyl)-3-[6-(5-hydroxymethyl-4'-methanesulfonyl-biphenyl-3-yloxy)-hexyl]-phenoxy}-butyric acid ethyl ester

생성물 1

HCID 594968304-{2-(2-Ethoxycarbonyl-ethyl)-3-[6-(4'-methanesulfonyl-5-methoxymethyl-biphenyl-3-yloxy)-hexyl]-phenoxy}-butyric acid ethyl ester수율 79.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 4-{2-(2-ethoxycarbonyl-ethyl)-3-[6-(5-hydroxymethyl-4′-methanesulfonyl-biphenyl-3-yloxy)-hexyl]-phenoxy}-butyric acid ethyl ester (250 mg, 0.37 mmol) in DMF (5 mL) were added sodium hydride (29.9 mg, 0.75 mmol), and iodomethane (106.2 mg, 0.75 mmol) at room temperature. The resulting suspension was stirred for 15 h and then the excess sodium hydride was quenched by slow addition of water (5 mL). The mixture was diluted with 1.0N hydrochloric acid (25 mL) and the organic compound was extracted into ethyl acetate (2×25 mL). The combined extracts were washed with brine solution (50 mL) and dried over anhydrous magnesium sulfate. Filtration of the drying agent and removal of the solvent under vacuum afforded the crude residue which was purified by using an ISCO 40 g column to obtain 4-{2-(2-ethoxycarbonyl-ethyl)-3-[6-(4′-methanesulfonyl-5-methoxymethyl-biphenyl-3-yloxy)-hexyl]-phenoxy}-butyric acid ethyl ester (200 mg, 78%) as a light brown oil: ES(+)-HRMS m/e calcd for C38H50O9S (M+Na)+ 705.3068. found 705.3069.

후처리

  1. customthe excess sodium hydride was quenched by slow addition of water (5 mL)
  2. additionThe mixture was diluted with 1.0N hydrochloric acid (25 mL)
  3. extractionthe organic compound was extracted into ethyl acetate (2×25 mL)
  4. washThe combined extracts were washed with brine solution (50 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationFiltration of the drying agent and removal of the solvent under vacuum
  7. customafforded the crude residue which
  8. customwas purified

출처 및 근거

ORD 기록
ord-5ddf247f4d0b4154b1bd67ad35bd025d
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08088936B2

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