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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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5-methyl-1H-pyrazole-3-carboxylic acid → HCID 20304344, 화합물

HRID 1732669
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HRID 1732669 반응식
Cl[C:2](OCC)=O.C[C:8]1[NH:12][N:11]=[C:10]([C:13]([OH:15])=O)[CH:9]=1.Cl.[NH2:17][CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][C:28]([O:30]CC)=[O:29])=[CH:22][CH:21]=1.[OH-].[Na+]>C(O)C.C(N(CC)CC)C.O1CCCC1>[CH3:2][C:10]1([C:13]([NH:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][C:28]([OH:30])=[O:29])=[CH:22][CH:21]=2)=[O:15])[N:11]=[N:12][CH:8]=[CH:9]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 98225-methyl-1H-pyrazole-3-carboxylic acidHCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 20463439Ethyl 3-[4-(2-aminoethyl)phenyl]propanoate--hydrogen chloride (1/1)

생성물 1

HCID 20304344HCID 20304344, 화합물수율 22%

시약·촉매·용매 3

HCID 702
Ethanol
용매
HCID 8028Tetrahydrofuran용매
HCID 8471Triethylamine용매

실험 절차

1.27 ml. triethylamino and 0.85 ml. ethyl chloroformate are added at -10° C. to a solution of 1.12 g. 5-methylpyrazole-3-carboxylic acid in 25 ml. anhydrous tetrahydrofuran. After 15 minutes, a further 1.27 ml. triethylamine is added and then 2.57 g. ethyl β-[4-(2-aminoethyl)-phenyl]-propionate hydrochloride. The reaction mixture is stirred for 1 hour at +20° C., filtered with suction and the filtered is evaporated and the residue taken up in methylene chloride. After extraction with 2% hydrochloric acid, 2 N aqueous sodium hydroxide solution and neutralization, the solution is dried and evaporated. The crude ester thus obtained is heated under reflux for 1 hour with 0.6 g. sodium hydroxide in 30 ml. ethanol. After cooling, the precipitated sodium salt is filtered off with suction, dissolved in water and carefully acidified. The precipitate obtained is filtered off and recrystallized from 20% ethanol. There is obtained β-{4-[2-(5-methylpyrazole- 5-carboxamido)-ethyl]-phenyl}-propionic acid in a yield of 22% of theory; m.p. 202°-205° C.

후처리

  1. filtrationfiltered with suction
  2. customthe filtered is evaporated
  3. extractionAfter extraction with 2% hydrochloric acid, 2 N aqueous sodium hydroxide solution and neutralization
  4. customthe solution is dried
  5. customevaporated
  6. customThe crude ester thus obtained
  7. temperatureis heated
  8. temperatureunder reflux for 1 hour with 0.6 g
  9. temperatureAfter cooling
  10. filtrationthe precipitated sodium salt is filtered off with suction
  11. dissolutiondissolved in water
  12. customThe precipitate obtained
  13. filtrationis filtered off
  14. customrecrystallized from 20% ethanol

출처 및 근거

ORD 기록
ord-b8fa5235ac394e36b620466849e75def
출처 데이터셋
uspto-grants-1980_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04238506

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