Ethanol → HCID 57595540, compound

HRID 1786075Notes

Reaction equation

HRID 1786075 reaction equation
C([O:3][C:4]([C:6]1[N:7]([CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([N:23]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[C@H:26]([N:33]([C:41](=[O:43])[CH3:42])[C:34]4[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=4)[CH2:25][C@@H:24]3[CH3:44])=[O:22])=[CH:17][CH:16]=2)[CH:8]=[CH:9][N:10]=1)=[O:5])C.C(O)C.[OH-].[Na+]>O1CCCC1>[C:41]([N:33]([C:34]1[CH:35]=[CH:36][C:37]([Cl:40])=[CH:38][CH:39]=1)[C@H:26]1[C:27]2[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=2)[N:23]([C:21]([C:18]2[CH:19]=[CH:20][C:15]([O:14][CH2:13][CH2:12][CH2:11][N:7]3[CH:8]=[CH:9][N:10]=[C:6]3[C:4]([OH:5])=[O:3])=[CH:16][CH:17]=2)=[O:22])[C@@H:24]([CH3:44])[CH2:25]1)(=[O:43])[CH3:42]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 57595395HCID 57595395, compound

Product 1

HCID 57595540HCID 57595540, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(2S,4R)-1-[3-(4-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenoxy)-propyl]-1H-imidazole-2-carboxylic acid was prepared from (2S,4R)-1-[3-(4-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenoxy)-propyl]-1H-imidazole-2-carboxylic acid ethyl ester. The ester (0.100 g, 0.16 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 4 hours. The mixture was cooled to room temperature, acidified to form a white precipitate. The solid was filtered to give (2S,4R)-1-[3-(4-{4-[acetyl(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenoxy)-propyl]-1H-imidazole-2-carboxylic acid in 65% 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-9e46bdd784874040a700a6bd4b91755e
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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