Triethylamine → Methyl 1-[2-{3-[4-(1,1'-biphenyl-4-ylmethoxy)phenyl]propoxy}-5-(ethoxycarbonyl)-benzoyl]-4-piperidinecarboxylate

HRID 1782769ノート

反応式

HRID 1782769 の反応式
O.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.[C:19]1([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[CH:24]=[CH:23][C:22]([CH2:25][O:26][C:27]2[CH:32]=[CH:31][C:30]([CH2:33][CH2:34][CH2:35][O:36][C:37]3[CH:45]=[CH:44][C:43]([C:46]([O:48][CH2:49][CH3:50])=[O:47])=[CH:42][C:38]=3[C:39]([OH:41])=O)=[CH:29][CH:28]=2)=[CH:21][CH:20]=1.Cl.[NH:58]1[CH2:63][CH2:62][CH:61]([C:64]([O:66][CH3:67])=[O:65])[CH2:60][CH2:59]1>ClCCl.O>[C:19]1([C:51]2[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=2)[CH:24]=[CH:23][C:22]([CH2:25][O:26][C:27]2[CH:28]=[CH:29][C:30]([CH2:33][CH2:34][CH2:35][O:36][C:37]3[CH:45]=[CH:44][C:43]([C:46]([O:48][CH2:49][CH3:50])=[O:47])=[CH:42][C:38]=3[C:39]([N:58]3[CH2:63][CH2:62][CH:61]([C:64]([O:66][CH3:67])=[O:65])[CH2:60][CH2:59]3)=[O:41])=[CH:31][CH:32]=2)=[CH:21][CH:20]=1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 187838294-Piperidinecarboxylic acid, methyl ester, hydrochloride (1:1)HCID 57589042HCID 57589042、化合物

生成物 1

HCID 57589096Methyl 1-[2-{3-[4-(1,1'-biphenyl-4-ylmethoxy)phenyl]propoxy}-5-(ethoxycarbonyl)-benzoyl]-4-piperidinecarboxylate収率 96.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

75 mg of N-[(3-dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (EDC), 27 mg of 1-hydroxy-1H-benzotriazole hydrate (HOBT) and 40 mg of triethylamine, are successively added to a suspension of 100 mg of 2-{3-[4-(1,1′-biphenyl-4-ylmethoxy)phenyl]propoxy}-5-(ethoxycarbonyl)benzoic acid and 39 mg of methyl piperidine-4-carboxylate hydrochloride in 30 ml of dichloromethane. Water is added to the reaction mixture after 15 hours at room temperature. After phase separation, the aqueous phase is extracted with ethyl acetate. The combined dichloromethane and ethyl acetate phases are washed with saturated brine and dried over anhydrous sodium sulphate. Filtration and concentration result in a crude product which is purified by suction filtration through silica gel with cyclohexane/ethyl acetate 1:1 as mobile phase. 120 mg of product are obtained.

後処理

  1. customAfter phase separation
  2. extractionthe aqueous phase is extracted with ethyl acetate
  3. washThe combined dichloromethane and ethyl acetate phases are washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulphate
  5. filtrationFiltration and concentration
  6. customresult in a crude product which
  7. filtrationis purified by suction filtration through silica gel with cyclohexane/ethyl acetate 1:1 as mobile phase

出典と根拠

ORDレコード
ord-d2b43d784765443f96e992ce4337d8c8
出典データセット
uspto-grants-2009_03
特許番号
US07498460B2

反応ノート

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