Hydrochloric Acid → HCID 66636874, compound

HRID 469247Notes

Reaction equation

HRID 469247 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-58236a414ab0446c91d575476f8fd418
Source dataset
uspto-grants-2014_01
Patent number
US08629126B2

Reaction notes

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