Sodium Hydroxide → 4-Acetylamino-5-(3-methoxyphenyl)valeric acid

HRID 274076

Reaction equation

HRID 274076 reaction equation
[C:1]([NH:4][CH:5]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=1)[CH2:6][CH2:7][C:8]([O:10]C(C)(C)C)=[O:9])(=[O:3])[CH3:2].[OH-].[Na+]>O1CCOCC1.Cl>[C:1]([NH:4][CH:5]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=1)[CH2:6][CH2:7][C:8]([OH:10])=[O:9])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 20094840Tert-butyl 4-acetylamino-5-(3-methoxyphenyl)valerate

Product 1

HCID 200947844-Acetylamino-5-(3-methoxyphenyl)valeric acidYield 86.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of tert-butyl 4-acetylamino-5-(3-methoxyphenyl)valerate (508 mg) in 1,4-dioxane (2 ml), 4N hydrogen chloride in 1,4-dioxane (4 ml) was added and the solution was stirred for 1 hour. The solution was poured into ice water (6 ml) and the pH of the solution was adjusted to 12 with sodium hydroxide solution. The solution was washed successively with diisopropyl ether and ethyl acetate and the pH of the solution was adjusted to 1 with 6N hydrochloric acid. The solution was extracted with ethyl acetate and the extract was washed with brine, dried over anhydrous sodium sulfate, and evaporated in vacuo to give 4-acetylamino-5-(3-methoxyphenyl)valeric acid (362 mg).

Workup

  1. washThe solution was washed successively with diisopropyl ether and ethyl acetate
  2. extractionThe solution was extracted with ethyl acetate
  3. washthe extract was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-6ed3ce07efd2419ca22ddb8ad687b278
Source dataset
uspto-grants-1995_02
Patent number
US05387710

Linked notes

Loading…