Sodium triacetoxyborohydride → (E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)-benzylidene]-5-[1-(3-morpholin-4-ylphenyl)ethylamino]valeric acid ethyl ester

HRID 1362644

반응식

HRID 1362644 반응식
[CH2:1]([O:3][C:4](=[O:25])/[C:5](=[CH:10]/[C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH:21]=[C:20]([CH3:22])[N:19]=[CH:18]2)=[C:13]([O:23][CH3:24])[CH:12]=1)/[CH2:6][CH2:7][CH:8]=O)[CH3:2].[N:26]1([C:32]2[CH:33]=[C:34]([CH:38]([NH2:40])[CH3:39])[CH:35]=[CH:36][CH:37]=2)[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.C(O)(=O)C.C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:25])/[C:5](=[CH:10]/[C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH:21]=[C:20]([CH3:22])[N:19]=[CH:18]2)=[C:13]([O:23][CH3:24])[CH:12]=1)/[CH2:6][CH2:7][CH2:8][NH:40][CH:38]([C:34]1[CH:35]=[CH:36][CH:37]=[C:32]([N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[CH:33]=1)[CH3:39])[CH3:2]

참가 물질

8

반응물 4

HCID 5049666Sodium triacetoxyborohydrideHCID 167404951-(3-Morpholinophenyl)ethanamineHCID 86585896Sodium bicarbonate waterHCID 86602475(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]-5-oxovaleric acid ethyl ester

생성물 1

HCID 66960920(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)-benzylidene]-5-[1-(3-morpholin-4-ylphenyl)ethylamino]valeric acid ethyl ester수율 76.2%

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

To a methylene chloride (10 mL) solution of (E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)-benzylidene]-5-oxovaleric acid ethyl ester (173 mg) obtained in Example 398, 1-(3-morpholin-4-yl-phenyl)ethyl amine (157 mg) and acetic acid (0.1 mL) and sodium triacetoxy borohydride (214 mg) were added one by one. The reaction solution was agitated at room temperature for 1 hour, a saturated sodium bicarbonate water and ethyl acetate were added to the reaction solution, and the organic layer was partitioned. After the obtained organic layer was washed with a saturated saline solution, it was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (Carrier: Chromatorex NH, elution solvent: heptane-ethyl acetate=1:2), and 205 mg of the title compound was obtained. The physical properties of the compound are as follows.

후처리

  1. customthe organic layer was partitioned
  2. washAfter the obtained organic layer was washed with a saturated saline solution, it
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (Carrier: Chromatorex NH, elution solvent: heptane-ethyl acetate=1:2)

출처 및 근거

ORD 기록
ord-c6a954e7b3c943c3821188b7b6fb0398
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07880009B2

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