Hydrochloric Acid → HCID 46829833, compound

HRID 2094644Notes

Reaction equation

HRID 2094644 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:29]2[C:38]3[C:33](=[C:34]([C:40]#[N:41])[CH:35]=[C:36]([CH3:39])[CH:37]=3)[CH:32]=[CH:31][CH:30]=2)[C@@H:9]([C:13]2[CH:28]=[CH:27][C:16]([C:17]([NH:19][CH2:20][CH2:21][C:22]([O:24]CC)=[O:23])=[O:18])=[CH:15][CH:14]=2)[CH2:10][CH2:11][CH3:12])=[CH:4][CH:3]=1.C1COCC1.CO.[Li+].[OH-].Cl>CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:29]2[C:38]3[C:33](=[C:34]([C:40]#[N:41])[CH:35]=[C:36]([CH3:39])[CH:37]=3)[CH:32]=[CH:31][CH:30]=2)[C@@H:9]([C:13]2[CH:28]=[CH:27][C:16]([C:17]([NH:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])=[O:18])=[CH:15][CH:14]=2)[CH2:10][CH2:11][CH3:12])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 21899815MeOH tetrahydrofuranHCID 58468260HCID 58468260, compound

Product 1

HCID 46829833HCID 46829833, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl N-(4-{(1S)-1-[(4-chlorophenyl)(5-cyano-7-methyl-1-naphthyl)methyl]butyl}benzoyl)-β-alaninate (18 mg, 0.032 mmol) in 2:1 THF/MeOH (3 mL) at room temperature was added LiOH (2.0 N in water, 0.265 mL, 0.530 mmol). The mixture was stirred at room temperature for one hour. The mixture was acidified with 2.0 N HCl (aq) and diluted with EtOAc. The organic layer was washed twice with water, dried over sodium sulfate, filtered, then concentrated to afford the title product as a white solid. LC1 1.59 min. [M+H]+ 538.

Workup

  1. washThe organic layer was washed twice with water
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d6ddcd65372247aca432f7118aeeac48
Source dataset
uspto-grants-2013_05
Patent number
US08445538B2

Reaction notes

Loading…