Potassium Hydroxide → (2S,4R)-(4-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenoxy)-fluoro-acetic acid

HRID 1786029Notes

Reaction equation

HRID 1786029 reaction equation
C([O:3][C:4](=[O:38])[C@@H:5]([O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([N:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C@H:19]([N:26]([C:34](=[O:36])[CH3:35])[C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=3)[CH2:18][CH:17]2[CH3:37])=[O:15])=[CH:10][CH:9]=1)[F:6])C.[OH-].[K+]>CO.C1COCC1>[C:34]([N:26]([C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=1)[C@H:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:16]([C:14]([C:11]2[CH:12]=[CH:13][C:8]([O:7][C@@H:5]([F:6])[C:4]([OH:38])=[O:3])=[CH:9][CH:10]=2)=[O:15])[CH:17]([CH3:37])[CH2:18]1)(=[O:36])[CH3:35]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 86601699(2S,4R)-(4-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenoxy)-fluoro-acetic acid ethyl ester

Product 1

HCID 86601703(2S,4R)-(4-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenoxy)-fluoro-acetic acid

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

(2S,4R)-(4-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenoxy)-fluoro-acetic acid ethyl ester (100 mg) was dissolved in methanol/THF (1:1, 5 mL), and potassium hydroxide (1.0N, 1 mL) was added. After 1 hour, the reaction was acidified and extracted with methylene chloride. The organic layer was dried, filtered, and concentrated. The crude residue was purified by silica gel chromatography 100% ethyl acetate to 5% methanol/ethyl acetate gradient to afford the product.

Workup

  1. extractionextracted with methylene chloride
  2. customThe organic layer was dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude residue was purified by silica gel chromatography 100% ethyl acetate to 5% methanol/ethyl acetate gradient
  6. customto afford the product

Sources & evidence

ORD record
ord-41a8cfe9bf9b4d32a4294e6f1769bfda
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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