Acetic Acid → HCID 67774058, compound

HRID 1808798Notes

Reaction equation

HRID 1808798 reaction equation
[OH-].[Na+].ClC1C=CC(C([O:10][CH2:11][C@@H:12]([N:16]([CH3:26])[C:17](=[O:25])[C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[CH:13]([CH3:15])[CH3:14])=O)=CC=1.O.C(O)(=O)C>CO>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([C:17]([N:16]([C@@H:12]([CH:13]([CH3:15])[CH3:14])[CH2:11][OH:10])[CH3:26])=[O:25])=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 14798Sodium Hydroxide2×HCID 67772465HCID 67772465, compound

Product 1

HCID 67774058HCID 67774058, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

NaOH (2.35 ml, 8.93 mmol) was added to (S)-2-(4-chloro-N-methylbenzamido)-3-methylbutyl 4-chlorobenzoate (Compound C2.1) (3.2 g, 8.12 mmol) in MeOH. The resultant mixture was stirred at rt for 20 min. Additional NaOH (1.07 ml, 4.06 mmol) was added and the stirring continued for 1 h. To the mixture was water (5 mol) added and the resultant mixture was stirred 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, 3×50 mL), filtered through a phase separator and concentrated under reduced pressure to give the title compound (1.47 g, 71%). The obtained crude product was used without further purification. Mixture of rotamers: (600 MHz, CD3OD) δ 0.78-0.85, 0.95-0.99, 1.02-1.07, 1.78-1.86, 1.90-1.98, 2.84, 2.95, 3.35-3.40, 3.59-3.66, 3.68-3.77, 3.83-3.88, 4.28-4.34, 7.39-7.48. Total no of protons: 17. LCMS (M+H)+: 256.

Workup

  1. additionadded
  2. customThe solvent was removed
  3. additionDCM (50 mL) was added
  4. washThe organic phase was washed with NaHCO3 (saturated, 3×50 mL)
  5. filtrationfiltered through a phase separator
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c78fcc9675a544c0972a2f1865bd7f07
Source dataset
uspto-grants-2013_01
Patent number
US08361998B2

Reaction notes

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