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Hydrochloric Acid → Finafloxacin hydrochloride

HRID 2302230
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HRID 2302230 반응식
[C:1]([C:3]1[C:4](F)=[C:5]([F:22])[CH:6]=[C:7]2[C:12]=1[N:11]([CH:13]1[CH2:15][CH2:14]1)[CH:10]=[C:9]([C:16]([O:18]CC)=[O:17])[C:8]2=[O:21])#[N:2].[C@H:24]12[CH2:32][NH:31][CH2:30][C@@H:29]1[NH:28][CH2:27][CH2:26][O:25]2.O.[OH-].[Li+].[ClH:36]>C(#N)C.O.C(N(CC)CC)C>[ClH:36].[C:1]([C:3]1[C:4]([N:31]2[CH2:32][C@H:24]3[C@@H:29]([NH:28][CH2:27][CH2:26][O:25]3)[CH2:30]2)=[C:5]([F:22])[CH:6]=[C:7]2[C:12]=1[N:11]([CH:13]1[CH2:14][CH2:15]1)[CH:10]=[C:9]([C:16]([OH:18])=[O:17])[C:8]2=[O:21])#[N:2]
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참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 15069982(4aS,7aS)-octahydropyrrolo[3,4-b][1,4]oxazineHCID 18417531Ethyl 8-cyano-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate

생성물 1

HCID 11662028Finafloxacin hydrochloride

시약·촉매·용매 3

HCID 962
Water
용매
HCID 6342Acetonitrile용매
HCID 8471Triethylamine용매

실험 절차

200 mg (0.63 mmol) of ethyl 8-cyano-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate are stirred under argon at 40-45° C. for 2 hours with 97 mg (0.75 mmol) of (1S,6S)-2-oxa-5,8-diazabicyclo[4.3.0]nonane and 0.17 ml of triethylamine in 3 ml of acetonitrile. All volatile components are removed in vacuo, the residue is treated with water, insoluble material is filtered off and the filtrate is extracted with dichloromethane. The organic phase is dried over sodium sulphate and then concentrated in vacuo. The resulting residue is dissolved in 6 ml of tetrahydrofuran and 2 ml of water and treated with 30 mg (0.72 mmol) of lithium hydroxide monohydrate. After stirring at room temperature for 16 hours, the mixture is acidified with dil. hydrochloric acid and the resulting precipitate is filtered off with suction and dried.

후처리

  1. customAll volatile components are removed in vacuo
  2. additionthe residue is treated with water, insoluble material
  3. filtrationis filtered off
  4. extractionthe filtrate is extracted with dichloromethane
  5. dry with materialThe organic phase is dried over sodium sulphate
  6. concentrationconcentrated in vacuo
  7. dissolutionThe resulting residue is dissolved in 6 ml of tetrahydrofuran
  8. filtrationthe resulting precipitate is filtered off with suction
  9. customdried

출처 및 근거

ORD 기록
ord-8e511d8626114cb6b25eb1cd345ff9cd
출처 데이터셋
uspto-grants-2002_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06432948B1

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