Ethanol → HCID 57595443, compound

HRID 1785984Notes

Reaction equation

HRID 1785984 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH:9]([O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([N:21]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[C@H:24]([N:31]([C:39](=[O:41])[CH3:40])[C:32]4[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=4)[CH2:23][C@@H:22]3[CH3:42])=[O:20])=[CH:15][CH:14]=2)[CH2:8][CH2:7]1)=[O:5])C.C(O)C.[OH-].[Na+]>O1CCCC1>[C:39]([N:31]([C:32]1[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=1)[C@H:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:21]([C:19]([C:16]2[CH:17]=[CH:18][C:13]([O:12][CH:9]3[CH2:10][CH2:11][CH:6]([C:4]([OH:5])=[O:3])[CH2:7][CH2:8]3)=[CH:14][CH:15]=2)=[O:20])[C@@H:22]([CH3:42])[CH2:23]1)(=[O:41])[CH3:40]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 57595493HCID 57595493, compound

Product 1

HCID 57595443HCID 57595443, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(2S,4R)-4-(4-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenoxy)-cyclohexanecarboxylic acid ethyl ester (0.060, 0.10 mmol) was hydrolyzed to the acid by dissolving in tetrahydrofuran and ethanol and sodium hydroxide (1N) was added. The mixture was stirred at room temperature 10 hours. The mixture was cooled to room temperature, acidified to form a white precipitate. The solid was filtered to give (2S,4R)-4-(4-{4-[acetyl(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenoxy)-cyclohexanecarboxylic acid as a white powder in 62% yield.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customto form a white precipitate
  3. filtrationThe solid was filtered

Sources & evidence

ORD record
ord-4a9379993f7c4b638179dca48983574c
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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