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Carbamide Peroxide → 4-((1-(tert-butoxycarbonyl)-4-carbamoylpiperidin-4-yl)methyl)-1-tert-butyl-1H-pyrazole-3-carboxylic acid

HRID 537112
ノート
印刷プレビュー

反応式

HRID 537112 の反応式
[C:1]([N:5]1[CH:9]=[C:8]([CH2:10][C:11]2([C:24]#[N:25])[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)[C:7]([C:26]([O:28]CC)=[O:27])=[N:6]1)([CH3:4])([CH3:3])[CH3:2].NC(N)=[O:33].OO>CO.[OH-].[Na+]>[C:20]([O:19][C:17]([N:14]1[CH2:15][CH2:16][C:11]([CH2:10][C:8]2[C:7]([C:26]([OH:28])=[O:27])=[N:6][N:5]([C:1]([CH3:3])([CH3:4])[CH3:2])[CH:9]=2)([C:24](=[O:33])[NH2:25])[CH2:12][CH2:13]1)=[O:18])([CH3:23])([CH3:22])[CH3:21]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 31294Carbamide PeroxideHCID 67491622tert-butyl 4-((1-tert-butyl-3-(ethoxycarbonyl)-1H-pyrazol-4-yl)methyl)-4-cyanopiperidine-1-carboxylate

生成物 1

HCID 674914864-((1-(tert-butoxycarbonyl)-4-carbamoylpiperidin-4-yl)methyl)-1-tert-butyl-1H-pyrazole-3-carboxylic acid収率 93.9%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 14798
Sodium Hydroxide
溶媒

実験手順

To a 0° C. solution of tert-butyl 4-((1-tert-butyl-3-(ethoxycarbonyl)-1H-pyrazol-4-yl)methyl)-4-cyanopiperidine-1-carboxylate (455 mg, 1.09 mmol) in methanol (11 mL) was added a solution of urea-hydrogen peroxide (1.05 g, 10.9 mmol) in 1 M aqueous sodium hydroxide (10.9 mL), dropwise. After stirring for 18 hours at room temperature, volatiles were removed under reduced pressure and the resultant slurry was taken up in water (50 mL), acidified with 2 N aqueous hydrochloric acid and extracted with ethyl acetate (2×50 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated to yield 4-((1-(tert-butoxycarbonyl)-4-carbamoylpiperidin-4-yl)methyl)-1-tert-butyl-1H-pyrazole-3-carboxylic acid (418 mg) as a colorless solid. −APCI (M−H) 407.3; 1H NMR (400 MHz, DMSO-d6, δ): 12.33 (br. s., 1H), 7.47 (s, 1H), 7.11 (br. s., 1H), 6.99 (s, 1H), 3.59 (d, J=13.3 Hz, 2H), 2.89 (s, 2H), 2.77 (m, 2H), 1.84 (m, 2H), 1.44 (s, 9H), 1.31 (s, 9H), 1.16 (m, 2H).

後処理

  1. customvolatiles were removed under reduced pressure
  2. extractionextracted with ethyl acetate (2×50 mL)
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-bb9040f98f5b48e6af4ab8802e9a8a06
出典データセット
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08859773B2

反応ノート

読み込み中…

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