Triethylamine → (2R,4R)-2-[2-Fluoro-4-(3-methyl-pyrazol-1-yl)-phenylcarbamoyl]-4-methoxy-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 2217574ノート

反応式

HRID 2217574 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][CH3:14])[CH2:10][C@@H:9]1[C:15]([OH:17])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:18][C:19]1[CH:24]=[C:23]([N:25]2[CH:29]=[CH:28][C:27]([CH3:30])=[N:26]2)[CH:22]=[CH:21][C:20]=1[NH2:31].CCOC1N(C(OCC)=O)C2C(=CC=CC=2)C=C1.CCN(CC)CC>C(Cl)(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][CH3:14])[CH2:10][C@@H:9]1[C:15](=[O:17])[NH:31][C:20]1[CH:21]=[CH:22][C:23]([N:25]2[CH:29]=[CH:28][C:27]([CH3:30])=[N:26]2)=[CH:24][C:19]=1[F:18])=[O:7])([CH3:2])([CH3:3])[CH3:4]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 11459222(2R,4R)-1-[(tert-butoxy)carbonyl]-4-methoxypyrrolidine-2-carboxylic acidHCID 221815262-Fluro-4-(3-methyl-pyrazol-1-yl)phenylamine

生成物 1

HCID 68805326(2R,4R)-2-[2-Fluoro-4-(3-methyl-pyrazol-1-yl)-phenylcarbamoyl]-4-methoxy-pyrrolidine-1-carboxylic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒2 回

実験手順

(2R,4R)-4-methoxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (0.350 g, 1.427 mmol), aniline 1 (0.273 g, 1.427 mmol) and EEDQ (0.529 g, 2.140 mmol) were dissolved in CHCl3 (30 mL). Et3N (0.6 mL, 4.281 mmol) was added and the reaction mixture was heated at reflux for 18 h. The mixture was allowed to cool and diluted with CHCl3 (100 mL) and washed with 5% HCl, 0.5 N NaOH, water and brine (40 mL each), the organic extract was dried over MgSO4, filtered and the solvent removed to give a pale tan foam. The crude product was used for the next step without purification. MS: APCI (AP+): 419.2 (M)+, (AP−): 417.2 (M)−.

後処理

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 18 h
  3. temperatureto cool
  4. washwashed with 5% HCl, 0.5 N NaOH, water and brine (40 mL each)
  5. extractionthe organic extract
  6. dry with materialwas dried over MgSO4
  7. filtrationfiltered
  8. customthe solvent removed
  9. customto give a pale tan foam
  10. customThe crude product was used for the next step without purification

出典と根拠

ORDレコード
ord-aec5810b2ffe491ea8b9443d16fdcac4
出典データセット
uspto-grants-2008_08
特許番号
US07407974B2

反応ノート

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