Sodium Hydroxide → 1-(tert-butoxycarbonyl)-4-((3-iodo-1-isopropyl-1H-pyrazol-4-yl)methyl)piperidine-4-carboxylic acid

HRID 711030노트

반응식

HRID 711030 반응식
[I:1][C:2]1[C:6]([CH2:7][C:8]2([C:21]([O:23]CC)=[O:22])[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[CH:5][N:4]([CH:26]([CH3:28])[CH3:27])[N:3]=1.[OH-].[Na+]>CO>[C:17]([O:16][C:14]([N:11]1[CH2:12][CH2:13][C:8]([CH2:7][C:6]2[C:2]([I:1])=[N:3][N:4]([CH:26]([CH3:27])[CH3:28])[CH:5]=2)([C:21]([OH:23])=[O:22])[CH2:9][CH2:10]1)=[O:15])([CH3:20])([CH3:18])[CH3:19]

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 674915631-tert-butyl 4-ethyl 4-((3-iodo-1-isopropyl-1H-pyrazol-4-yl)methyl)piperidine-1,4-dicarboxylate

생성물 1

HCID 674914961-(tert-butoxycarbonyl)-4-((3-iodo-1-isopropyl-1H-pyrazol-4-yl)methyl)piperidine-4-carboxylic acid수율 100.1%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of 1-tert-butyl 4-ethyl 4-((3-iodo-1-isopropyl-1H-pyrazol-4-yl)methyl)piperidine-1,4-dicarboxylate (455 mg, 0.9 mmol) in methanol (20 mL) was added 2 N NaOH (5 mL). After stirring for 18 hours at room temperature, the methanol was removed under reduced pressure and the resultant slurry was taken up in 20 mL water, acidified with 2 N HCl and extracted with ethyl acetate (2×30 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated to yield 1-(tert-butoxycarbonyl)-4-((3-iodo-1-isopropyl-1H-pyrazol-4-yl)methyl)piperidine-4-carboxylic acid (430 mg) as a colorless solid. −APCI (M−H) 476.1; 1H NMR (400 MHz, CDCl3, δ): 7.11 (s, 1H), 4.45 (dquin, J=13.4, 6.7 Hz, 1H), 3.95 (br. s., 2H), 2.91 (m, 2H), 2.69 (s, 2H), 2.08 (m, 2H), 1.47 (m, 8H).

후처리

  1. customthe methanol was removed under reduced pressure
  2. extractionextracted with ethyl acetate (2×30 mL)
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-b33496cbb69d420682ae9d0224852fed
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181252B2

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