Potassium Hydroxide → (R)-2-(6-Chloro-3,4-dihydroquinolin-1(2H)-yl)-4-methylpentanoic acid

HRID 1715914Notes

Reaction equation

HRID 1715914 reaction equation
[OH-].[K+].[Cl:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]([C@H:14]([CH2:20][CH:21]([CH3:23])[CH3:22])[C:15]([O:17]CC)=[O:16])[CH2:9][CH2:8][CH2:7]2.ClC1C=C2C(=CC=1)N([C@@H](C(C)C)C(O)=O)CCC2>CO>[Cl:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]([C@H:14]([CH2:20][CH:21]([CH3:23])[CH3:22])[C:15]([OH:17])=[O:16])[CH2:9][CH2:8][CH2:7]2

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 59465663(R)-ethyl 2-(6-chloro-3,4-dihydroquinolin-1(2H)-yl)-4-methylpentanoateHCID 59466246(S)-2-(6-chloro-3,4-dihydroquinolin-1(2H)-yl)-3-methylbutanoic acid

Product 1

HCID 59466371(R)-2-(6-Chloro-3,4-dihydroquinolin-1(2H)-yl)-4-methylpentanoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

KOH (2.0 M in H2O, 0.34 mL, 0.68 mmol) was added to a 0° C., stirring solution of (R)-ethyl 2-(6-chloro-3,4-dihydroquinolin-1(2H)-yl)-4-methylpentanoate (50 mg, 0.17 mmol) in MeOH (0.32 mL). The reaction was allowed to warm to RT and stirred overnight. Due to the instability of the final product as a solid, the solution containing (S)-2-(6-chloro-3,4-dihydroquinolin-1(2H)-yl)-3-methylbutanoic acid was used for the next step without further work up. LC/MS (10%/99% CH3CN (0.035% TFA)/H2O (0.05% TFA), m/z: M+1 obs=282.3; tR=3.72 min.

Sources & evidence

ORD record
ord-566f0f0dd5134dc3b8561a018fd01544
Source dataset
uspto-grants-2010_09
Patent number
US07799822B2

Reaction notes

Loading…