Hydrochloric Acid → HCID 66934634, compound

HRID 1365504Notes

Reaction equation

HRID 1365504 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@:8]([C:21]2[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[C:23]([F:31])[CH:22]=2)([NH:14][C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:9][C:10]([O:12]C)=[O:11])=[N:6][CH:7]=1.[Li+].[OH-].Cl>C1COCC1.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@:8]([C:21]2[CH:26]=[C:25]([C:27]([F:30])([F:28])[F:29])[CH:24]=[C:23]([F:31])[CH:22]=2)([NH:14][C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:9][C:10]([OH:12])=[O:11])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58921306HCID 58921306, compound

Product 1

HCID 66934634HCID 66934634, compoundYield 88.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

(S)-methyl 3-(5-chloropyridin-2-yl)-3-(3-fluoro-5-(trifluoromethyl)phenyl)-3-pivalamidopropanoate (1.04 g, 2.16 mmol, prepared as described in Procedure 11) was dissolved in THF (30 mL) at room temperature. A4M LiOH solution was added (20 mL) and the reaction mixture stirred at RT for 14 h. The RM was diluted with EtOAc (ca. 100 mL) and the pH adjusted to pH1-2 by addition of 1 M HCl. The organic portion was separated and the aqueous washed with EtOAc (ca.2×20 mL). The combined organic portions were dried over anhydrous Na2SO4, decanted and concentrated yielding (S)-3-(5-chloropyridin-2-yl)-3-(3-fluoro-5-(trifluoromethyl)phenyl)-3-pivalamidopropanoic acid as a colorless oil (0.856 g, 85% yield) LCMS: 1.90 min [M+1] 467.2 (2 min gradient, MeOH/H2O 0.1% TFA).

Workup

  1. customThe organic portion was separated
  2. washthe aqueous washed with EtOAc (ca.2×20 mL)
  3. dry with materialThe combined organic portions were dried over anhydrous Na2SO4
  4. customdecanted
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b5149b8de6ac4422a1dfe0803658e562
Source dataset
uspto-grants-2011_02
Patent number
US07888376B2

Reaction notes

Loading…