Pyridine → HCID 178472472、化合物

HRID 1713833ノート

反応式

HRID 1713833 の反応式
Cl[C:2](=[O:7])[C:3]([O:5][CH3:6])=[O:4].[NH2:8][C:9]1[CH:26]=[CH:25][C:12]([O:13][CH:14]2[CH2:19][CH2:18][CH:17]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:16][CH2:15]2)=[CH:11][CH:10]=1.N1C=CC=CC=1>C(Cl)Cl>[CH3:6][O:5][C:3](=[O:4])[C:2]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([O:13][C@H:14]2[CH2:19][CH2:18][C@H:17]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:16][CH2:15]2)=[CH:25][CH:26]=1)=[O:7]

参加物

5

反応物 3

HCID 1049PyridineHCID 79846Methyl chloroglyoxylateHCID 57452913HCID 57452913、化合物

生成物 1

HCID 178472472HCID 178472472、化合物収率 91%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Methyl chlorooxoacetate (45 μL, 0.48 mmol) was added in one portion to a stirred solution of ethyl 4-(4-aminophenoxy)cyclohexanecarboxylate (127 mg, 0.48 mmol) and pyridine (47 μL, 0.58 mmol) in DCM (5 mL) and the reaction mixture was stirred for 30 minutes. Volatile material was removed by evaporation and the residue was taken up in EtOAc (40 mL) and an aqueous solution of hydrochloric acid (1M, 20 mL) was added. The layers were separated and the organic layer was washed with brine (10 mL), dried and concentrated in vacuo to give the title compound (152 mg, 91%) as a solid; 1H NMR (CDCl3) δ1.19 (3H, t), 1.39-1.45 (2H, m), 1.48-1.56 (2H, m), 1.97-2.03 (2H, m), 2.08-2.12 (2H, m), 2.23-2.31 (1H, m), 3.89 (3H, s), 4.07 (2H, q), 4.11-4.14 (1H, m), 6.80-6.84 (2H, d), 7.44-7.48 (2H, d), 8.66 (1H, s); MS m/e MR+ 350.

後処理

  1. customVolatile material was removed by evaporation
  2. additionan aqueous solution of hydrochloric acid (1M, 20 mL) was added
  3. customThe layers were separated
  4. washthe organic layer was washed with brine (10 mL)
  5. customdried
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-0a94fa33971f47d8a8bde8177a30bd6e
出典データセット
uspto-grants-2010_09
特許番号
US07795283B2

反応ノート

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