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Potassium Carbonate → 1-(4-t-Butoxycarbonyl-benzyl)-5-propyl-1H-pyrazole-3-carboxylic acid ethyl ester

HRID 919346
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HRID 919346 반응식
[C:1]([O:5][C:6](=[O:15])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13]Br)=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:16]([O:18][C:19]([C:21]1[CH:25]=[C:24]([CH2:26][CH2:27][CH3:28])[NH:23][N:22]=1)=[O:20])[CH3:17].C(=O)([O-])[O-].[K+].[K+].[Li+].[Cl-]>CN(C=O)C>[CH2:16]([O:18][C:19]([C:21]1[CH:25]=[C:24]([CH2:26][CH2:27][CH3:28])[N:23]([CH2:13][C:10]2[CH:11]=[CH:12][C:7]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:15])=[CH:8][CH:9]=2)[N:22]=1)=[O:20])[CH3:17]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 11430Potassium CarbonateHCID 433294Lithium ChlorideHCID 7365260ethyl 3-propyl-1H-pyrazole-5-carboxylateHCID 11414578Tert-butyl 4-(bromomethyl)benzoate

생성물 1

HCID 598309141-(4-t-Butoxycarbonyl-benzyl)-5-propyl-1H-pyrazole-3-carboxylic acid ethyl ester

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

To the recovered intermediate (19a) (1.4 g, 5 mmol, 1.0 eq) dissolved into 15 mL DMF, was added 5-propyl-1H-pyrazole-3-carboxylic acid ethyl ester (910 mg, 5.0 mmol, 1.0 eq) and potassium carbonate (0.8 g, 5.5 mmol, 1.1 eq) and the mixture was stirred at room temperature for 16 hours. The mixture was then added to 50 mL of 10% aq. LiCl solution and extracted with 50 mL EtOAc. The organic was dried over MgSO4, and concentrated under reduced pressure to yield intermediate (19b) and its regioisomer in a 1:1 ratio. The recovered regioisomers were dissolved into 25 mL MeOH. To this was added 10 mL of 1M NaOH and the mixture was stirred at room temperature over night. The mixture was acidified with acetic acid and concentrated under reduced pressure. The recovered oil was purified by preparatory HPLC, producing the desired regioisomer of the title compound as a white solid TFA salt after lyophilization (230 mg). 1H NMR (DMSO) 0.89 (t, 3H), 1.52 (s, 9H), 5.71 (s, 2H), 6.71 (s, 1H), 7.15 (d, 2H), 7.83 (d, 2H), 13.28 (br s, 1H).

후처리

  1. extractionextracted with 50 mL EtOAc
  2. dry with materialThe organic was dried over MgSO4
  3. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-6a84fcba839740d39a90891efb55896f
출처 데이터셋
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09273008B2

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