HCID 89580778, compound → HCID 89580527, compound

HRID 1479770Notes

Reaction equation

HRID 1479770 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][CH:7]([C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15]C)=[O:14])=[CH:11][CH:10]=1)[CH3:8])(=[O:3])[CH3:2]>O1CCCC1.O>[C:1]([NH:4][CH2:5][CH2:6][CH:7]([C:9]1[CH:10]=[CH:11][C:12]([C:13]([OH:15])=[O:14])=[CH:17][CH:18]=1)[CH3:8])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 89580778HCID 89580778, compound

Product 1

HCID 89580527HCID 89580527, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

Methyl 4-(4-acetamidobutan-2-yl)benzoate (0.23 g, 0.9 mmol) was dissolved in a mixture of in tetrahydrofuran (10 mL) and water (50 mL), then stirred at 45° C. for 12 hours, after the completion of the reaction, the organic phase was removed under reduced pressure, to the residue was added 1 N hydrochloride to adjust the pH 3-4, then the mixture was extracted with ethyl acetate (10 mL×3), collected the organic phase and dried over Sodium sulfate anhydrous, removed the solvent to afford 4-(4-acetamidobutan-2-yl)benzoic acid (0.21 g, 100%) as a pale yellow oil and directly used in next step. LRMS (M+H+) m/z: calcd for 235.28. found 235.

Workup

  1. customafter the completion of the reaction
  2. customthe organic phase was removed under reduced pressure, to the residue
  3. additionwas added 1 N hydrochloride
  4. extractionthe mixture was extracted with ethyl acetate (10 mL×3)
  5. customcollected the organic phase
  6. dry with materialdried over Sodium sulfate anhydrous
  7. customremoved the solvent

Sources & evidence

ORD record
ord-8273765d1bcb47b0b5da7c423b92f10b
Source dataset
uspto-grants-2016_08
Patent number
US09409865B2

Reaction notes

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