Lithium Hydroxide → HCID 68921116, compound

HRID 1785922Notes

Reaction equation

HRID 1785922 reaction equation
FC1C=CC(C(Cl)=O)=CC=1.C[O:12][C:13](=[O:46])[CH:14]=[CH:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([N:24]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C@H:27]([N:34]([C:42](=[O:44])[CH3:43])[C:35]3[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=3)[CH2:26][C@@H:25]2[CH3:45])=[O:23])=[CH:18][CH:17]=1.[Li+].[OH-]>C1COCC1.CO>[C:42]([N:34]([C:35]1[CH:36]=[CH:37][C:38]([Cl:41])=[CH:39][CH:40]=1)[C@H:27]1[C:28]2[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:24]([C:22]([C:19]2[CH:20]=[CH:21][C:16]([CH:15]=[CH:14][C:13]([OH:46])=[O:12])=[CH:17][CH:18]=2)=[O:23])[C@@H:25]([CH3:45])[CH2:26]1)(=[O:44])[CH3:43]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 678794-Fluorobenzoyl chlorideHCID 68917517HCID 68917517, compound

Product 1

HCID 68921116HCID 68921116, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

(2S,4R)-3-(4-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenyl)-acrylic acid was prepared following general procedure C, substituting 3-(4-chlorocarbonyl-phenyl)-acrylic acid methyl ester for 4-fluorobenzoyl chloride. The ester was hydrolyzed as follows. To a solution of (2S,4R)-3-(4-{4-[acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenyl)-acrylic acid methyl ester (112 mg, 0.239 mmol) in THF/MeOH (2 ml, 2 ml) was added LiOH (4 ml: 1.0 M in H2O). Upon consumption of the starting unit (1 hour), the mixture was neutralized with aq. HCl (1.0 M), partioned with EtOAc (10 ml) and separated. The organic layer was separated and concentrated whereby the resulting oil was subjected to silica gel chromatography (2% MeOH in EtOAc to 10% MeOH in EtOAc) to afford the title compound (110 mg, 99%).

Workup

  1. custom(2S,4R)-3-(4-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenyl)-acrylic acid was prepared
  2. customUpon consumption of the starting unit (1 hour)
  3. customseparated
  4. customThe organic layer was separated
  5. concentrationconcentrated whereby the resulting oil

Sources & evidence

ORD record
ord-6265fcbda6b84c8bb5e65fe278b1e988
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

Loading…