Hydrochloric Acid → HCID 58732805, compound

HRID 553016Notes

Reaction equation

HRID 553016 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:41][CH3:42])[C:9]([C@@H:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([C:21]([C:23]3[CH:39]=[CH:38][C:26]([O:27][CH2:28][CH2:29][C:30]([F:37])([F:36])[C:31]([O:33]CC)=[O:32])=[CH:25][CH:24]=3)=[O:22])[C@@H:13]([CH3:40])[CH2:12]2)=[O:10])=[CH:4][CH:3]=1.[OH-].[Li+].CO.Cl>C1COCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:41][CH3:42])[C:9]([C@@H:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([C:21]([C:23]3[CH:24]=[CH:25][C:26]([O:27][CH2:28][CH2:29][C:30]([F:37])([F:36])[C:31]([OH:33])=[O:32])=[CH:38][CH:39]=3)=[O:22])[C@@H:13]([CH3:40])[CH2:12]2)=[O:10])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 131728939HCID 131728939, compound

Product 1

HCID 58732805HCID 58732805, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (±)-trans-ethyl 4-(4-{[4-{[(4-chlorophenyl)(ethyl)amino]carbonyl}-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenoxy)-2,2-difluorobutanoate (190 mg, 0.32 mmol) in THF (4.4 mL) was added a solution of lithium hydroxide (15.2 mg, 0.63 mmol) in water (2 mL). To the resulting mixture was added methanol (2 mL) and the reaction stirred 18 hours at room temperature. The reaction mixture pH was adjusted to 2 via addition of 1N hydrochloric acid and extracted with ethyl acetate (3×25 mL). The combined organic layers were washed with brine, dried over magnesium sulfate and concentrated in vacuo to yield (±)-trans-4-(4-{[4-{[(4-chlorophenyl)(ethyl)amino]carbonyl}-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenoxy)-2,2-difluorobutanoic acid. 1H-NMR (CDCl3) δ: 0.96 (d, 3H), 1.08 (t, 3H), 1.61-1.74 (m, 1H), 2.34-2.56 (m, 3H), 3.52-3.68 (m, 1H), 3.72-3.88 (m, 2H), 4.00-4.14 (m, 2H), 4.93-5.11 (m, 1H), 6.42-6.51 (m, 1H), 6.65-6.82 (m, 4H), 6.83-6.92 (m, 1H), 7.16-7.29 (m, 2H), 7.37-7.50 (m, 4H). MS m/z: 571 (M+1).

Workup

  1. extractionextracted with ethyl acetate (3×25 mL)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1620b55dd45647568e30319662e8039e
Source dataset
uspto-grants-2011_05
Patent number
US07951950B2

Reaction notes

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