Hydrochloric Acid → 3-Acetyl-2-{2-[(tert-butoxycarbonyl)amino]ethoxy}-5-chloro-6-methylbenzoic acid

HRID 626822Notes

Reaction equation

HRID 626822 reaction equation
[C:1]([C:4]1[C:9]([O:10][CH2:11][CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[C:8]([CH:21]=[O:22])[C:7]([CH3:23])=[C:6]([Cl:24])[CH:5]=1)(=[O:3])[CH3:2].[OH-:25].[Na+].Cl>CO.O.OO.NC(N)=O>[C:1]([C:4]1[C:9]([O:10][CH2:11][CH2:12][NH:13][C:14]([O:15][C:16]([CH3:18])([CH3:19])[CH3:17])=[O:20])=[C:8]([C:7]([CH3:23])=[C:6]([Cl:24])[CH:5]=1)[C:21]([OH:25])=[O:22])(=[O:3])[CH3:2]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 86697512tert-Butyl [2-(6-acetyl-4-chloro-2-formyl-3-methylphenoxy)ethyl]carbamate

Product 1

HCID 866975173-Acetyl-2-{2-[(tert-butoxycarbonyl)amino]ethoxy}-5-chloro-6-methylbenzoic acidYield 84%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 31294Carbamide PeroxideSolvent2×

Procedure

tert-Butyl [2-(6-acetyl-4-chloro-2-formyl-3-methylphenoxy)ethyl]carbamate (85 mg, 0.24 mmol) was stirred in methanol (7 mL) and 1.0 M sodium hydroxide in water (2.7 mL) and urea hydrogen peroxide addition compound (200 mg, 2 mmol) was added. Additional urea hydrogen peroxide addition compound (20 mg) and 1.0 M sodium hydroxide in water (0.5 mL) were added and the mixture was stirred for 3 more hours. 1 N HCl was added to pH 5 and the methanol was evaporated. The mixture was extracted with ethyl acetate, washed with brine, dried over sodium sulfate, filtered and evaporated to give the desired compound (75 mg, 84%). LCMS calculated for C17H22ClNO6Na (M+Na)+: m/z=394.1; found: 393.9.

Workup

  1. additionwas added
  2. additionwere added
  3. customthe methanol was evaporated
  4. extractionThe mixture was extracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-31dbbc89fc6b4db3ba645a35cef5762c
Source dataset
uspto-grants-2016_04
Patent number
US09309251B2

Reaction notes

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