Pyridine → HCID 178472472, 화합물

HRID 1713833노트

반응식

HRID 1713833 반응식
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]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 79846Methyl chloroglyoxylateHCID 57452913HCID 57452913, 화합물

생성물 1

HCID 178472472HCID 178472472, 화합물수율 91%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0a94fa33971f47d8a8bde8177a30bd6e
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795283B2

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