Potassium Hydroxide → 3-(Acetylamino)-2-[4-(tert-butoxycarbonyl)phenyl]propanoic acid

HRID 1919904Notes

Reaction equation

HRID 1919904 reaction equation
[C:1]([NH:4][CH2:5][CH:6]([C:11]1[CH:23]=[CH:22][C:14]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:13][CH:12]=1)[C:7]([O:9]C)=[O:8])(=[O:3])[CH3:2].[OH-].[K+]>C1COCC1.CO.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[C:1]([NH:4][CH2:5][CH:6]([C:11]1[CH:12]=[CH:13][C:14]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:22][CH:23]=1)[C:7]([OH:9])=[O:8])(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 57611947Tert-butyl 4-{1-[(acetylamino)methyl]-2-methoxy-2-oxoethyl}benzoate

Product 1

HCID 576119543-(Acetylamino)-2-[4-(tert-butoxycarbonyl)phenyl]propanoic acid

Reagents, catalysts & solvents 3

HCID 311Citric AcidSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 4-{1-[(acetylamino)methyl]-2-methoxy-2-oxoethyl}benzoate (530 mg, 1.65 mmol) in THF (9 mL) and MeOH (3 mL) was added KOH (1N, 1.98 mL, 1.98 mmol). After stirring at room temperature for 1 h, the mixture was diluted with 0.5 M citric acid and extracted with EtOAc. The organic layer was washed with water and brine, dried (MgSO4), and concentrated to yield 3-(acetylamino)-2-[4-(tert-butoxycarbonyl)phenyl]propanoic acid as a white powder. MS (ESI) calcd [M+Na]+ 330.1, found 330.1.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9f225ad7867c489f97684d4bae114919
Source dataset
uspto-grants-2012_05
Patent number
US08168658B2

Reaction notes

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