Hydrochloric Acid → HCID 11613876, compound

HRID 1785948Notes

Reaction equation

HRID 1785948 reaction equation
C[O:2][C:3](=[O:41])[C:4]([CH3:40])([CH3:39])[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][C@@H:17]2[CH3:37])=[O:15])=[CH:10][C:9]=1[F:38].[OH-].[Li+].Cl>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:12]=[CH:13][C:8]([O:7][CH2:6][CH2:5][C:4]([CH3:40])([CH3:39])[C:3]([OH:41])=[O:2])=[C:9]([F:38])[CH:10]=2)=[O:15])[C@@H:17]([CH3:37])[CH2:18]1)(=[O:36])[CH3:35]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 57595479HCID 57595479, compound

Product 1

HCID 11613876HCID 11613876, compound

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}-2-fluoro-phenoxy)-2,2-dimethyl-butyric acid methyl ester (100 mg) was dissolved in methanol/THF (1:1, 5 mL), and lithium hydroxide (1.0N, 1 mL) was added. After 1 hour, the reaction was acidified (HCl) and extracted from with methylene chloride. The organic layer was dried, filtered, and concentrated. The crude residue was purified by silica gel chromatography ethyl acetate-5% MeOH/ethylacetate gradient) to afford the product.

Workup

  1. extractionextracted from 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/ethylacetate gradient)
  6. customto afford the product

Sources & evidence

ORD record
ord-00607726e7474170b55eb44769e4da10
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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