Hydrochloric Acid → HCID 22227947, 화합물

HRID 1526947노트

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HRID 1526947 반응식
[CH3:1][C:2]1[N:6]([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:15]([O:17]C)=[O:16].O.[OH-].[Li+].O1CCCC1.Cl>O.CO>[CH3:1][C:2]1[N:6]([CH2:7][CH2:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:5]=[CH:4][C:3]=1[C:15]([OH:17])=[O:16]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 89740836methyl 5-methyl-1-phenethyl-1H-pyrazole-4-carboxylate

생성물 1

HCID 22227947HCID 22227947, 화합물수율 36.2%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

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온도
20 °C

실험 절차

A mixture of methyl 5-methyl-1-phenethyl-1H-pyrazole-4-carboxylate (177 mg, 0.72 mmol), lithium hydroxide monohydrate (111 mg, 2.62 mmol), tetrahydrofuran (5 mL), methanol (1 mL) and water (1 mL) was stirred at 20° C. for 4 hours. The mixture was acidified to pH=1 with concentrated hydrochloric acid and then extracted with ethyl acetate (15 mL×3). The combined organic phase was dried by sodium sulfate, and then filtered. The filtrate was concentrated in vacuum and separated by HPLC (condition: column AD-H (20 mm*250 mm*5 μm), hexane:ethanol (0.2% DEA)=50:50, flow rate: 13 mL/min) to give 5-methyl-1-phenethyl-1H-pyrazole-4-carboxylic acid (60 mg, 36%). LRMS (M+H+) m/z: calcd. 230.11; found 230.

후처리

  1. extractionextracted with ethyl acetate (15 mL×3)
  2. dry with materialThe combined organic phase was dried by sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuum
  5. customseparated by HPLC (condition: column AD-H (20 mm*250 mm*5 μm), hexane:ethanol (0.2% DEA)=50:50, flow rate: 13 mL/min)

출처 및 근거

ORD 기록
ord-66c8306ad5fe4b81849db35b2d939e17
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09085583B2

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