Lithium Hydroxide → HCID 21106878, compound

HRID 1765114Notes

Reaction equation

C([O:3][C:4]([C:6]1[C:15](=[O:16])[N:14]2[C:9]([C:10]([CH3:41])=[C:11]([N:18]3[CH2:22][CH2:21][CH:20]([C:23]4([N:26]([CH:28]5[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30][CH2:29]5)[CH3:27])[CH2:25][CH2:24]4)[CH2:19]3)[C:12]([F:17])=[CH:13]2)=[C:8]([CH:42]2[CH2:44][CH2:43]2)[CH:7]=1)=[O:5])C.[Li+].[OH-]>C(O)C.O>[C:37]([O:36][C:34]([N:31]1[CH2:30][CH2:29][CH:28]([N:26]([CH3:27])[C:23]2([CH:20]3[CH2:21][CH2:22][N:18]([C:11]4[C:12]([F:17])=[CH:13][N:14]5[C:9]([C:10]=4[CH3:41])=[C:8]([CH:42]4[CH2:43][CH2:44]4)[CH:7]=[C:6]([C:4]([OH:5])=[O:3])[C:15]5=[O:16])[CH2:19]3)[CH2:25][CH2:24]2)[CH2:33][CH2:32]1)=[O:35])([CH3:40])([CH3:38])[CH3:39]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 8-(3-{1-[(1-tert-butoxycarbonyl-piperidin-4-yl)-methyl-amino]-cyclopropyl}-pyrrolidin-1-yl)-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid ethyl ester (15 g, 24 mmol) in ethanol (200 mL) was added the solution of LiOH (10 g, 238 mmol) in water (100 mL) in a round bottom flask. The solution was heated at 60° C. for one hour. The resulting solution was partitioned between dichloromethane (400 mL) and saturated aqueous NH4Cl (200 mL) and well shaken. The organic layer was separated, washed with brine, dried over sodium sulfate and concentrated in vacuo to yield a yellow solid (14 g). This was used without further purification.

Workup

customThe resulting solution was partitioned between dichloromethane (400 mL) and saturated aqueous NH4Cl (200 mL)
customThe organic layer was separated
washwashed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-e5caf9e80cb44f9db1772368082ac889
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07226931B2

Reaction notes

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