Hydrochloric Acid → HCID 66636874, compound

HRID 1094205Notes

Reaction equation

HRID 1094205 reaction equation
[CH:1]1([NH:7][C:8]2[CH:17]=[C:16]3[C:11]([C:12](=[O:35])[C:13]([NH:23][C:24](=[O:34])[CH2:25][C@@H:26]4[C:30](=[O:31])[O:29]C(C)(C)[O:27]4)=[CH:14][N:15]3[CH:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[CH:10][C:9]=2[F:36])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[OH-].[Na+]>C1COCC1>[CH:1]1([NH:7][C:8]2[CH:17]=[C:16]3[C:11]([C:12](=[O:35])[C:13]([NH:23][C:24](=[O:34])[CH2:25][C@@H:26]([OH:27])[C:30]([OH:31])=[O:29])=[CH:14][N:15]3[CH:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[CH:10][C:9]=2[F:36])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 14798Sodium HydroxideHCID 66636973HCID 66636973, compound

Product 1

HCID 66636874HCID 66636874, compoundYield 9.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 1.0 ml THF-1.0 ml methanol mixed solution of 130 mg of N-[7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl]-2-[(4R)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]acetamide was added 0.3 ml of 1 M hydrochloric acid, followed by overnight stirring at room temperature. Then, 0.8 ml of aqueous 1M sodium hydroxide solution was added, followed by overnight stirring at room temperature. The resulting reaction mixture was neutralized with 1 M hydrochloric acid, and then the insoluble materials were collected by filtration and purified by silica gel column chromatography to obtain 11 mg of (2R)-4-{[7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl]amino}-2-hydroxy-4-oxobutanoic acid.

Workup

  1. waitfollowed by overnight
  2. stirringstirring at room temperature
  3. customThe resulting reaction mixture
  4. filtrationthe insoluble materials were collected by filtration
  5. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-90272072ace94480b25d4dd1627bc8b9
Source dataset
uspto-grants-2012_03
Patent number
US08133882B2

Reaction notes

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