HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Lithium hydroxide, monohydrate → 3-[(2S)-1-(Difluoromethoxy)propan-2-yl]oxy-5-[5-(dimethylcarbamoyl)pyrazin-2-yl]oxy-benzoic acid

HRID 2425490
Notes
Print preview

Reaction equation

HRID 2425490 reaction equation
O.[OH-].[Li+].[F:4][CH:5]([F:33])[O:6][CH2:7][C@@H:8]([O:10][C:11]1[CH:12]=[C:13]([CH:18]=[C:19]([O:21][C:22]2[CH:27]=[N:26][C:25]([C:28](=[O:32])[N:29]([CH3:31])[CH3:30])=[CH:24][N:23]=2)[CH:20]=1)[C:14]([O:16]C)=[O:15])[CH3:9]>O.C1COCC1>[F:33][CH:5]([F:4])[O:6][CH2:7][C@@H:8]([O:10][C:11]1[CH:12]=[C:13]([CH:18]=[C:19]([O:21][C:22]2[CH:27]=[N:26][C:25]([C:28](=[O:32])[N:29]([CH3:30])[CH3:31])=[CH:24][N:23]=2)[CH:20]=1)[C:14]([OH:16])=[O:15])[CH3:9]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59205092Methyl 3-[(2S)-1-(difluoromethoxy)propan-2-yl]oxy-5-[5-(dimethylcarbamoyl)pyrazin-2-yl]oxy-benzoate

Product 1

HCID 592050903-[(2S)-1-(Difluoromethoxy)propan-2-yl]oxy-5-[5-(dimethylcarbamoyl)pyrazin-2-yl]oxy-benzoic acidYield 75.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 8028
Tetrahydrofuran
Solvent

Procedure

Lithium hydroxide monohydrate (45 mg, 1.06 mol) in water (5 mL) was added to a solution of methyl 3-[(2S)-1-(difluoromethoxy)propan-2-yl]oxy-5-[5-(dimethylcarbamoyl)pyrazin-2-yl]oxy-benzoate (0.3 g, 0.71 mmol) in THF (10 mL) and stirred at RT for 20 hours. The THF was removed in vacuo and the aqueous layer was washed with ethyl acetate (50 mL) to remove any impurities. The aqueous layer was acidified and extracted into ethyl acetate (2×50 mL) then the combined organics washed with brine (50 mL), dried (MgSO4) and the solvent removed in vacuo to give the desired compound (0.22 g).

Workup

  1. customThe THF was removed in vacuo
  2. washthe aqueous layer was washed with ethyl acetate (50 mL)
  3. customto remove any impurities
  4. extractionextracted into ethyl acetate (2×50 mL)
  5. washthe combined organics washed with brine (50 mL)
  6. dry with materialdried (MgSO4)
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-01b87c7f407d495b8248a4f968096cb7
Source dataset
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07964725B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes