Hydrogen chloride-ethyl acetate → HCID 68415707, compound

HRID 40009Notes

Reaction equation

HRID 40009 reaction equation
C(OC([N:8]([CH2:33][C:34]1[CH:39]=[CH:38][C:37]([CH3:40])=[C:36]([F:41])[CH:35]=1)[CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][N:17]2[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([O:27][CH3:28])[CH:25]=3)[N:20]=[CH:19][C:18]2=[O:29])[CH:11]([C:30]([OH:32])=[O:31])[CH2:10]1)=O)(C)(C)C.[ClH:42].C(OCC)(=O)C>C(OCC)(=O)C>[ClH:42].[F:41][C:36]1[CH:35]=[C:34]([CH:39]=[CH:38][C:37]=1[CH3:40])[CH2:33][NH:8][CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][N:17]2[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([O:27][CH3:28])[CH:25]=3)[N:20]=[CH:19][C:18]2=[O:29])[CH:11]([C:30]([OH:32])=[O:31])[CH2:10]1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetate2×HCID 59398421HCID 59398421, compound

Product 1

HCID 68415707HCID 68415707, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 5 mL of a methanol solution containing 80 mg of methyl 4-((tert-butoxycarbonyl) (3-fluoro-4-methybenzyl)amino)-1-(2-(7-methoxy-2-oxoquinoxalin-1(2H)-yl)ethyl)piperidine-2-carboxylate, 0.2 mL of 2 mol/L aqueous sodium hydroxide solution was added at room temperature, and stirred for 2.5 hours. Further, 0.2 mL of 2 mol/L aqueous sodium hydroxide solution and 0.5 mL of water were added, stirred at the sane temperature for 4 hour and 40 min, and allowed to stand overnight. The solvent was removed under reduced pressure, and the reaction mixture was adjusted to pH 7.0 with 2 mol/L hydrochloric acid. To the mixture, water and ethyl acetate were added, the organic layer was separated, washed with aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to give 31 mg of 4-((tert-butoxycarbonyl) (3-fluoro-4-methybenzyl)amino)-1-(2-(7-methoxy-2-oxoquinoxalin-1(2H)-yl)ethyl)piperidine-2-carboxylic acid as a yellow solid. (2) To 5 mL of an ethyl acetate solution containing 31 mg of 4-((tert-butoxycarbonyl)(3-fluoro-4-methybenzyl)amino)-1-(2-(7-methoxy-2-oxoquinoxalin-1(2H)-yl)ethyl)piperidine-2-carboxylic acid, 0.1 mL of 4 mol/L hydrogen chloride/ethyl acetate solution was added at room temperature, and stirred for 6 hours and 40 min, further, 0.1 mL of 4 mol/L hydrogen chloride/ethyl acetate solution was added, and stirred for 3.5 hours. The resulting solid was filtered to give 30 mg of 4-((3-fluoro-4-methybenzyl)amino)-1-(2-(7-methoxy-2-oxoquinoxalin-1(2H)-yl)ethyl)piperidine-2-carboxylic acid hydrochloride as a yellow solid.

Workup

  1. additionwas added at room temperature
  2. stirringstirred for 3.5 hours
  3. filtrationThe resulting solid was filtered

Sources & evidence

ORD record
ord-f471ed0c12554beda56c7ada453afdb5
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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