Sodium Hydroxide → (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)-4-[4-((3S)-3-carboxymorpholino)-2-butynyl]piperazine

HRID 584242Notes

Reaction equation

HRID 584242 reaction equation
[F:1][C:2]([F:46])([F:45])[C:3]1[CH:4]=[C:5]([CH:38]=[C:39]([C:41]([F:44])([F:43])[F:42])[CH:40]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]#[C:16][CH2:17][N:18]2[CH2:23][CH2:22][O:21][CH2:20][C@H:19]2[C:24]([O:26]CC)=[O:25])[CH2:10][C@H:9]1[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([CH3:36])=[C:32]([CH3:37])[CH:31]=1)=[O:7].[OH-].[Na+]>C(O)C>[F:44][C:41]([F:42])([F:43])[C:39]1[CH:38]=[C:5]([CH:4]=[C:3]([C:2]([F:1])([F:46])[F:45])[CH:40]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]#[C:16][CH2:17][N:18]2[CH2:23][CH2:22][O:21][CH2:20][C@H:19]2[C:24]([OH:26])=[O:25])[CH2:10][C@H:9]1[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([CH3:36])=[C:32]([CH3:37])[CH:31]=1)=[O:7]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57253530HCID 57253530, compound

Product 1

HCID 86588523(2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)-4-[4-((3S)-3-carboxymorpholino)-2-butynyl]piperazineYield 64.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)-4-[4-((3S)-3-ethoxycarbonylmorpholino)-2-butynyl]piperazine (0.42 g) in ethanol (30 ml) was added 1N sodium hydroxide solution (30 ml) and the whole was stirred at room temperature for 2 hours. The solvent was removed under reduced pressure and the residual aqueous solution was neutralized with conc. hydrochloric acid. The solution was extracted with dichloromethane. The extract was dried over magnesium sulfate and evaporated in vacuo to give (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)-4-[4-((3S)-3-carboxymorpholino)-2-butynyl]piperazine (0.26 g) as an oil.

Workup

  1. customThe solvent was removed under reduced pressure
  2. extractionThe solution was extracted with dichloromethane
  3. dry with materialThe extract was dried over magnesium sulfate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-3c608db9e8ca4184892a959971f9703b
Source dataset
uspto-grants-2005_08
Patent number
US06924278B2

Reaction notes

Loading…