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Sodium Hydroxide → 2-Adamantan-1-ylmethyl-5-phenyl-1h-pyrrole-3-carboxylic acid

HRID 1018301
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HRID 1018301 반응식
C([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[NH:8][C:7]=1[CH2:17][C:18]12[CH2:27][CH:22]3[CH2:23][CH:24]([CH2:26][CH:20]([CH2:21]3)[CH2:19]1)[CH2:25]2)=[O:5])C.[OH-].[Na+]>C(O)C>[C:18]12([CH2:17][C:7]3[NH:8][C:9]([C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=4)=[CH:10][C:6]=3[C:4]([OH:5])=[O:3])[CH2:25][CH:24]3[CH2:23][CH:22]([CH2:21][CH:20]([CH2:26]3)[CH2:19]1)[CH2:27]2
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참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 117175262-Adamantan-1-ylmethyl-5-phenyl-1h-pyrrole-3-carboxylic acid ethyl ester

생성물 1

HCID 113820842-Adamantan-1-ylmethyl-5-phenyl-1h-pyrrole-3-carboxylic acid수율 95.5%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of the product of step b (750 mg, 2.06 mmol) in ethanol (45 ml) was added sodium hydroxide (5 ml of 6.0M solution). The mixture was heated at reflux for 48 h, it was allowed to cool to room temperature and concentrated to small volume under reduced pressure. The concentrated solution was diluted with 2M hydrochloric acid (40 ml), the precipitated solid was filtered, washed with water and dried to afford the acid (660 mg, 94%). 1H NMR (300 MHz, CDCl3) 11.5 (1H, br s), 8.26 (1H, br s), 7.48 (2H, m), 7.40 (2H, m), 7.26 (1H, m), 6.94 (1H, d), 2.87 92H, s), 1.97 (3H, br s), 1.63 (12H, m).

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 48 h
  3. concentrationconcentrated to small volume under reduced pressure
  4. additionThe concentrated solution was diluted with 2M hydrochloric acid (40 ml)
  5. filtrationthe precipitated solid was filtered
  6. washwashed with water
  7. customdried

출처 및 근거

ORD 기록
ord-721e89b93ae94c7b9ac7220275d5d532
출처 데이터셋
uspto-grants-2002_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06479531B1

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