Sodium Hydroxide → 5-Cycloheptylmethyl-2-naphthalen-2-yl-1H-imidazole-4-carboxylic Acid

HRID 1018308노트

반응식

HRID 1018308 반응식
C([O:3][C:4]([C:6]1[N:7]=[C:8]([C:19]2[CH:28]=[CH:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=2)[NH:9][C:10]=1[CH2:11][CH:12]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:5])C.[OH-].[Na+]>C(O)C.O>[CH:12]1([CH2:11][C:10]2[NH:9][C:8]([C:19]3[CH:28]=[CH:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:20]=3)=[N:7][C:6]=2[C:4]([OH:5])=[O:3])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1

참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 116394325-Cycloheptylmethyl-2-naphthalen-2-yl-1H-imidazole-4-carboxylic Acid Ethyl Ester

생성물 1

HCID 115593315-Cycloheptylmethyl-2-naphthalen-2-yl-1H-imidazole-4-carboxylic Acid수율 96%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

To a suspension of the product of step b (1.73 g, 4.62 mmol) in ethanol (25 ml) was added the solution of sodium hydroxide (1.29 g, 32.3 mmol) in water (5 ml). The reaction mixture was heated under reflux for 48 h, allowed to cool to room temperature and concentrated under reduced pressure. The aqueous solution was diluted with water (30 ml) and acidified to pH=2 with 1M hydrochloric acid. The precipitate was collected by filtration, washed with water, and dried to afford the product as an off-white solid (1.53 g, 96%). 1H NMR (300 MHz, d6-DMSO) 8.77 (1H, s), 8.24-7.98 (4H, m), 7.64 (2H, m), 2.91 and 2.64 (2H, 2×d), 2.03 (1H, m), 1.69-1.24 (12H, m).

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 48 h
  3. concentrationconcentrated under reduced pressure
  4. additionThe aqueous solution was diluted with water (30 ml)
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with water
  7. customdried

출처 및 근거

ORD 기록
ord-feab367d94774c8486d3fbdee4865e9b
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06479531B1

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