Fleroxacin → HCID 14781964, 화합물

HRID 1728915

반응식

HRID 1728915 반응식
[O:1]=[C:2]1[N:9]2[CH:4]([S:5][CH2:6][CH:7]=[C:8]2[C:10]([OH:12])=[O:11])[CH:3]1[NH:13][C:14](=[O:23])[CH2:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[CH3:24]N([Si](C)(C)C)C(=O)C(F)(F)F.[I:36][Si](C)(C)C.[F:41][C:42]1[CH:43]=[C:44]2[C:49](=[C:50]([F:59])[C:51]=1[N:52]1[CH2:57][CH2:56][N:55]([CH3:58])[CH2:54][CH2:53]1)[N:48]([CH2:60][CH2:61][F:62])[CH:47]=[C:46]([C:63]([OH:65])=[O:64])[C:45]2=[O:66]>CO.C(#N)C.C(Cl)Cl>[I-:36].[C:63]([C:46]1[C:45](=[O:66])[C:44]2[C:49](=[C:50]([F:59])[C:51]([N:52]3[CH2:53][CH2:54][N+:55]([CH2:24][C:7]4[CH2:6][S:5][C@H:4]5[N:9]([C:2](=[O:1])[C@H:3]5[NH:13][C:14](=[O:23])[CH2:15][O:16][C:17]5[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=5)[C:8]=4[C:10]([OH:12])=[O:11])([CH3:58])[CH2:56][CH2:57]3)=[C:42]([F:41])[CH:43]=2)[N:48]([CH2:60][CH2:61][F:62])[CH:47]=1)([OH:65])=[O:64]

참가 물질

8

반응물 4

HCID 3357FleroxacinHCID 32510N-methyl-N-(trimethylsilyl)trifluoroacetamide2회HCID 85247Trimethylsilyl iodideHCID 14286988HCID 14286988, 화합물

생성물 1

HCID 14781964HCID 14781964, 화합물

시약·촉매·용매 3

HCID 887Methanol용매HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

실험 절차

Under an argon atmosphere, a mixture of 406 mg (1 mmol) of [6R-trans]-3-(acetyloxy)methyl]-8-oxo-7-[(phenoxyacetyl)amino]-5-thia-1-azabicyclo[4.2.0]-oct-2-en-2-carboxylic acid, 2 mL of dry methylene chloride, a nd 0.60 mL (3 mmol) of N-methyl-N-(trimethylsilyl)trifluoroacetamide (MSTFA) was stirred for one hour: 0.28 mL (2 mmol) of iodotrimethylsilane was then added, and the mixture stirred for 2 hours. The solution was then concentrated to dryness under reduced pressure, and the residual oil dissolved in 2 mL of acetonitrile. Five drops of anhydrous THF were added, and the mixture was stirred for 5-10 minutes. A solution prepared from 111 mg (0.3 mmol) of 6,8-difluoro-1-(2-fluoroethyl)-1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid, 0.11 mL (0.6 mmol) of MSTFA and 1 mL of acetonitrile was added, and stirring was continued for 2 hours. The mixture was chilled in ice, and approximately 100 mg of methanol were added. The solid which precipitated was filtered, washed with acetonitrile, and dried under reduced pressure to obtain the title compound: NMR (Me2SO-d6) δ 3.15 (s, 3H, NCH3), 3.45-3.85 (m, 9H, 4 x NCH2 and CH of SCH2), 3.95 (d, 1H, J gem=16.5 Hz, CH of SCH2), 4.39 and 4.77 (AB, 2H, J gem=13 Hz, NCH2). 4.61 and 4.64 (AB, 2H, J gem=15 Hz, OCH2CO), 4.83-5.07 (m, 4H, NCH2CH2F), 5.24 (d, 1H, J=5Hz, CH), 5.82 (dd, 1H, J=5 and 7 Hz, CH), 6.95 (d, 2H, J=8 Hz, Ar), 6.97 (t, 1H, J=8 Hz, Ar), 7.29 (t, 2H, J=8 Hz), 7.96 (d, 1 H, J=12 Hz, Ar), 8.91 (s, 1H, =CH--), 9.18 (d, 1H, J=7 Hz, NH); IR (KBr) 3400, 1788, 1728, 1700, 1612, cm-1 ; mass spectrum m/z 716 (cation).

후처리

  1. concentrationThe solution was then concentrated to dryness under reduced pressure
  2. dissolutionthe residual oil dissolved in 2 mL of acetonitrile
  3. additionFive drops of anhydrous THF were added
  4. stirringthe mixture was stirred for 5-10 minutes
  5. additionwas added
  6. stirringstirring
  7. waitwas continued for 2 hours
  8. temperatureThe mixture was chilled in ice
  9. customThe solid which precipitated
  10. filtrationwas filtered
  11. washwashed with acetonitrile
  12. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-5ac05a6645054790a62e5ee9c02f204a
출처 데이터셋
uspto-grants-1994_07
특허 번호
US05329002

연결된 노트

불러오는 중…