HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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
Notes
Print preview

Reaction equation

HRID 251863 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 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

Product 1

HCID 66861539
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

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-1df2353abbc84dcb87334821f9425966
Source dataset
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07867992B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes