Ethanol → HCID 57595529, compound

HRID 1786021Notes

Reaction equation

HRID 1786021 reaction equation
C[O:2][C:3]([C:5]1[O:6][C:7]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([N:20]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[C@H:23]([N:30]([C:38](=[O:40])[CH3:39])[C:31]4[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=4)[CH2:22][C@@H:21]3[CH3:41])=[O:19])=[CH:14][CH:13]=2)=[CH:8][CH:9]=1)=[O:4].C(O)C.[OH-].[Na+]>O1CCCC1>[C:38]([N:30]([C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=1)[C@H:23]1[C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:20]([C:18]([C:15]2[CH:16]=[CH:17][C:12]([O:11][CH2:10][C:7]3[O:6][C:5]([C:3]([OH:4])=[O:2])=[CH:9][CH:8]=3)=[CH:13][CH:14]=2)=[O:19])[C@@H:21]([CH3:41])[CH2:22]1)(=[O:40])[CH3:39]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 68921675HCID 68921675, compound

Product 1

HCID 57595529HCID 57595529, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(2S,4R)-5-(4-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenoxymethyl)-furan-2-carboxylic acid methyl ester (0.145 g, 0.25 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 rt, acidified to form a white precipitate. The solid was filtered to give (2S,4R)-5-(4-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenoxymethyl)-furan-2-carboxylic acid as a white solid.

Workup

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

Sources & evidence

ORD record
ord-02d179395a7c42c29f7a5b41e2967e41
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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