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

HRID 1786068Notes

Reaction equation

HRID 1786068 reaction equation
C[O:2][C:3](=[O:39])[C@@H:4]([CH3:38])[CH2:5][CH2:6][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.[OH-].[Li+]>CO.C1COCC1>[C:34]([N:26]([C:27]1[CH:28]=[CH:29][C:30]([Cl:33])=[CH:31][CH:32]=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:10]=[CH:9][C:8]([O:7][CH2:6][CH2:5][C@H:4]([CH3:38])[C:3]([OH:39])=[O:2])=[CH:13][CH:12]=2)=[O:15])[CH:17]([CH3:37])[CH2:18]1)(=[O:36])[CH3:35]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68922830(2S,4R)-4-(4-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenoxy)-2-methyl-butyric acid methyl ester

Product 1

HCID 68927083(2S,4R)-4-(4-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenoxy)-2-methyl-butyric acid

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

(2S,4R)-4-(4-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenoxy)-2-methyl-butyric acid methyl ester (100 mg) was dissolved in methanol/THF, and lithium hydroxide (1.0N, 2 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 ethyl acetate—5% MeOH/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 ethyl acetate—5% MeOH/ethyl acetate gradient)
  6. customto afford the product

Sources & evidence

ORD record
ord-fb6089441de048dca7c3b8795d3d1cdd
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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