Acetic Acid → HCID 67773903, compound

HRID 1808799Notes

Reaction equation

HRID 1808799 reaction equation
[Li+].[OH-].FC1C=C(C=CC=1F)C([O:9][CH2:10][C@@H:11]([N:15]([CH3:26])[C:16](=[O:25])[C:17]1[CH:22]=[CH:21][C:20]([F:23])=[C:19]([F:24])[CH:18]=1)[CH:12]([CH3:14])[CH3:13])=O.C(O)(=O)C.C([O-])(O)=O.[Na+]>CO>[F:24][C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][C:20]=1[F:23])[C:16]([N:15]([C@@H:11]([CH:12]([CH3:14])[CH3:13])[CH2:10][OH:9])[CH3:26])=[O:25]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 3939Lithium Hydroxide2×HCID 516892Sodium BicarbonateHCID 67776041HCID 67776041, compound

Product 1

HCID 67773903HCID 67773903, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

LiOH (25.7 mL, 12.83 mmol) was added to (S)-2-(3,4-difluoro-N-methylbenzamido)-3-methylbutyl 3,4-difluorobenzoate (Compound C2.2) (4 g, 8.56 mmol) in MeOH (40 mL). The resultant mixture was stirred at rt over night. Additional LiOH (10.27 mL, 10.27 mmol) was added and the stirring continued for 2 h. The mixture was neutralized by the addition of acetic acid. The solvent was removed and DCM (50 mL) was added. The organic phase was washed with NaHCO3 (saturated, 1×50 mol, 2×30 mL), dried (Na2SO4) and concentrated under reduced pressure to give the title compound (2.18 g, 99%). The obtained crude product was used without further purification.

Workup

  1. customThe solvent was removed
  2. additionDCM (50 mL) was added
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-785b03c5a7b841289f985f93ef6a2ee7
Source dataset
uspto-grants-2013_01
Patent number
US08361998B2

Reaction notes

Loading…