Methanol → 1-(4-Phenyl-3-carboxybutyl)-2-[(4-chlorophenoxy)methyl]-4-methylbenzimidazole

HRID 1383965

반응식

HRID 1383965 반응식
O1CCCC1.CO.C([O:10][C:11]([CH:13]([CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH2:14][CH2:15][N:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[C:24]([CH3:25])[C:19]=2[N:18]=[C:17]1[CH2:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)=[O:12])C.[OH-].[Li+]>C1(C)C=CC=CC=1.C(O)CCC.O>[C:36]1([CH2:35][CH:13]([C:11]([OH:12])=[O:10])[CH2:14][CH2:15][N:16]2[C:20]3[CH:21]=[CH:22][CH:23]=[C:24]([CH3:25])[C:19]=3[N:18]=[C:17]2[CH2:26][O:27][C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=2)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

참가 물질

8

반응물 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 211885961-[3-(Ethoxycarbonyl)-4-phenylbutyl]-2-[(4-chlorophenoxy)methyl]-4-methylbenzimidazole

생성물 1

HCID 211886901-(4-Phenyl-3-carboxybutyl)-2-[(4-chlorophenoxy)methyl]-4-methylbenzimidazole수율 145.1%

시약·촉매·용매 3

HCID 2631-Butanol용매HCID 962Water용매HCID 1140Toluene용매

실험 절차

To a mixture of tetrahydrofuran (84 ml), methanol (28 ml), and water (28 ml), were added 1-[3-(ethoxycarbonyl)-4-phenylbutyl]-2-[(4-chlorophenoxy)methyl]-4-methylbenzimidazole (3.05 g, 6.4 mmol) and lithium hydroxide (788 mg, 3 eq.). The resulting mixture was stirred overnight at room temperature and was then concentrated in vacuo to yield a white solid. This residue was taken into 250 ml of a 3:1 butanol:toluene solution. The organic fraction was washed once with 200 ml of water and then dried over magnesium sulfate. The solvents were removed in vacuo to yield 4.17 grams of tan solid, which was further purified by flash chromatography, eluting with a gradient solvent of 19:1 ethyl acetate:methanol to 9:1 ethyl acetate:methanol. The fractions containing the desired material were combined and concentrated under reduced pressure to yield 2.71 grams (94%) of the desired title product as a white solid.

후처리

  1. concentrationwas then concentrated in vacuo
  2. customto yield a white solid
  3. washThe organic fraction was washed once with 200 ml of water
  4. dry with materialdried over magnesium sulfate
  5. customThe solvents were removed in vacuo

출처 및 근거

ORD 기록
ord-6d16011b2c184ed6a8a1dafbe3921225
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06255494B1

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