Hydrochloric Acid → 4-[(R)-2-((S)-2-Cyclobutylcarbamoyl-pyrrolidin-1-yl)-1-methyl-2-oxo-ethoxy]-7-methyl-quinoline-2-carboxylic acid

HRID 1185561Notes

Reaction equation

HRID 1185561 reaction equation
C[O:2][C:3]([C:5]1[CH:14]=[C:13]([O:15][C@H:16]([CH3:31])[C:17]([N:19]2[CH2:23][CH2:22][CH2:21][C@H:20]2[C:24](=[O:30])[NH:25][CH:26]2[CH2:29][CH2:28][CH2:27]2)=[O:18])[C:12]2[C:7](=[CH:8][C:9]([CH3:32])=[CH:10][CH:11]=2)[N:6]=1)=[O:4].[OH-].[Na+].Cl>C1COCC1>[CH:26]1([NH:25][C:24]([C@@H:20]2[CH2:21][CH2:22][CH2:23][N:19]2[C:17](=[O:18])[C@@H:16]([CH3:31])[O:15][C:13]2[C:12]3[C:7](=[CH:8][C:9]([CH3:32])=[CH:10][CH:11]=3)[N:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:14]=2)=[O:30])[CH2:27][CH2:28][CH2:29]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 686020364-[(R)-2-((S)-2-Cyclobutylcarbamoyl-pyrrolidin-1-yl)-1-methyl-2-oxo-ethoxy]-7-methyl-quinoline-2-carboxylic acid methyl ester

Product 1

HCID 686006134-[(R)-2-((S)-2-Cyclobutylcarbamoyl-pyrrolidin-1-yl)-1-methyl-2-oxo-ethoxy]-7-methyl-quinoline-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6.30 g 4-[(R)-2-((S)-2-Cyclobutylcarbamoyl-pyrrolidin-1-yl)-1-methyl-2-oxo-ethoxy]-7-methyl-quinoline-2-carboxylic acid methyl ester in 14 ml THF were added 14.3 ml aqueous NaOH (1 M) and the reaction mixture was stirred for 4 h at RT. The reaction mixture was acidified with 15 ml 1 M HCl, concentrated to a volume of 25 ml and extracted with DCM to give the crude product after evaporation of the solvent. Yield: 5.00 g

Workup

  1. concentrationconcentrated to a volume of 25 ml
  2. extractionextracted with DCM

Sources & evidence

ORD record
ord-6e15283efe4a4590ba1ef8659b1f4857
Source dataset
uspto-grants-2014_03
Patent number
US08669266B2

Reaction notes

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