Water → 5-amino-7-fluoro-1-[2-(S)-fluoro-1-(R)-cyclopropyl]-1,4-dihydro-8-methyl-4-oxoquinoline-3-Carboxylic Acid

HRID 600871노트

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HRID 600871 반응식
[NH2:1][C:2]1[CH:11]=[C:10]([F:12])[C:9]([CH3:13])=[C:8]2[C:3]=1[C:4](=[O:23])[C:5]([C:18]([O:20]CC)=[O:19])=[CH:6][N:7]2[C@@H:14]1[CH2:16][C@@H:15]1[F:17].O.S(=O)(=O)(O)O>C(O)(=O)C>[NH2:1][C:2]1[CH:11]=[C:10]([F:12])[C:9]([CH3:13])=[C:8]2[C:3]=1[C:4](=[O:23])[C:5]([C:18]([OH:20])=[O:19])=[CH:6][N:7]2[C@@H:14]1[CH2:16][C@@H:15]1[F:17]

참가 물질

5

반응물 3

HCID 962Water2회HCID 1118Sulfuric AcidHCID 67270424Ethyl 5-amino-7-fluoro-1-[2-(S)-fluoro-1-(R)-cyclopropyl]-1,4-dihydro-8-methyl-4-oxoquinoline-3-carboxyl ate

생성물 1

HCID 672716015-amino-7-fluoro-1-[2-(S)-fluoro-1-(R)-cyclopropyl]-1,4-dihydro-8-methyl-4-oxoquinoline-3-Carboxylic Acid수율 82.3%

시약·촉매·용매 1

HCID 176Acetic Acid용매

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온도
120 °C

실험 절차

Ethyl 5-amino-7-fluoro-1-[2-(S)-fluoro-1-(R)-cyclopropyl]-1,4-dihydro-8-methyl-4-oxoquinoline-3-carboxylate (735 mg, 2.28 mmol) was dissolved in a 1:1 mixed solution (8 ml) of acetic acid:water, and after adding concentrated sulfuric acid (90 μl) thereto, it was stirred for 4 hours in an oil bath of 120° C. After cooling the reaction solution with ice, water (20 ml) was poured therein, and the mixed reaction solution was stirred at room temperature for 2 hours. The precipitated crystals were filtered out, washed with excess water, a small amount of cold ethanol and excess diethyl ether in that order, and then dried under a reduced pressure at 80° C. for 17 hours. 552 mg (82%) of the title compound was thereby obtained in the form of yellow crystals.

후처리

  1. additionwas poured
  2. customthe mixed reaction solution
  3. stirringwas stirred at room temperature for 2 hours
  4. filtrationThe precipitated crystals were filtered out
  5. washwashed with excess water
  6. dry with materiala small amount of cold ethanol and excess diethyl ether in that order, and then dried under a reduced pressure at 80° C. for 17 hours

출처 및 근거

ORD 기록
ord-b8556ed33a384ad7bfad3ff57897d494
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902226B2

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