Lithium Hydroxide → 1-Cyclopropyl-N-(2,4-dichlorobenzyl)-7-{(3RS,5SR)-4-[(2R)-2,3-dihydroxypropyl]-3,5-dimethylpiperazin-1-yl}-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxamide hydrochloride

HRID 251863

반응식

HRID 251863 반응식
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:24])=[C:11]([N:16]4[CH2:21][CH:20]([CH3:22])[NH:19][CH:18]([CH3:23])[CH2:17]4)[C:12]=3[O:14][CH3:15])[C:7](=[O:25])[C:6]([C:26]([NH:28][CH2:29][C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:31]=3[Cl:37])=[O:27])=[CH:5]2)[CH2:3][CH2:2]1.C([O:43][CH2:44][C@@H:45]1[O:47][CH2:46]1)(=O)CCC.C([O-])(=O)CCC.[OH-].[Li+]>>[ClH:36].[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:24])=[C:11]([N:16]4[CH2:17][CH:18]([CH3:23])[N:19]([CH2:46][C@@H:45]([OH:47])[CH2:44][OH:43])[CH:20]([CH3:22])[CH2:21]4)[C:12]=3[O:14][CH3:15])[C:7](=[O:25])[C:6]([C:26]([NH:28][CH2:29][C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:31]=3[Cl:37])=[O:27])=[CH:5]2)[CH2:3][CH2:2]1

참가 물질

5

반응물 4

HCID 3939Lithium HydroxideHCID 104775ButyrateHCID 2724536(2R)-Oxiran-2-ylmethyl butanoateHCID 668599621-Cyclopropyl-N-(2,4-dichlorobenzyl)-7-[(3RS,5SR)-3,5-dimethylpiperazin-1-yl]-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxamide

생성물 1

HCID 668615391-Cyclopropyl-N-(2,4-dichlorobenzyl)-7-{(3RS,5SR)-4-[(2R)-2,3-dihydroxypropyl]-3,5-dimethylpiperazin-1-yl}-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxamide hydrochloride

실험 절차

The title compound is prepared in analogy to Example 89 from Example 12 with (2R)-3-butanoyloxy-1,2-epoxypropane and subsequent hydrolysis of the butyrate with 1 equivalent of a 1M lithium hydroxide solution at 70° C. for 1 h. For the work-up the solvent is removed on a rotary evaporator, the residue is adjusted to a neutral pH using 1N hydrochloric acid and buffer pH 7 and extracted with dichloromethane. Purification takes place by RP-HPLC (Method 6).

후처리

  1. customFor the work-up the solvent is removed on a rotary evaporator
  2. extractionextracted with dichloromethane
  3. customPurification

출처 및 근거

ORD 기록
ord-1df2353abbc84dcb87334821f9425966
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07867992B2

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