Sodium Hydroxide → 3-(3-{[(tert-Butoxycarbonyl)amino]methyl}phenyl)propanoic acid

HRID 1838766Notes

Reaction equation

HRID 1838766 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[C:12]([CH2:16][CH2:17][C:18]([O:20]C)=[O:19])[CH:13]=[CH:14][CH:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>O1CCCC1>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[C:12]([CH2:16][CH2:17][C:18]([OH:20])=[O:19])[CH:13]=[CH:14][CH:15]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18752845HCID 18752845, compound

Product 1

HCID 222827283-(3-{[(tert-Butoxycarbonyl)amino]methyl}phenyl)propanoic acidYield 102.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 3.6 g of methyl 3-(3-tert-butyloxycarbonylaminomethylphenyl)propionate (C3) in 36 ml of tetrahydrofurane 14.8 ml of 1N aqueous sodium hydroxide solution are added and the mixture is stirred at RT for 2 days. After neutralization with 14.8 ml 1N hydrochloric acid solution and dilution with water the mixture is extracted three times with ethyl acetate. The combined extracts are dried over magnesium sulfate, filtered and the solvent removed in vacuo to give 3.5 g of the title compound as a brownish oil which solidifies on standing in a refrigerator. The mass spectrum shows the molecular peak MNH4+ at 297 Da.

Workup

  1. extractionAfter neutralization with 14.8 ml 1N hydrochloric acid solution and dilution with water the mixture is extracted three times with ethyl acetate
  2. dry with materialThe combined extracts are dried over magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-a201779365a141639a97b964a0e7ac87
Source dataset
uspto-grants-2004_01
Patent number
US06673786B1

Reaction notes

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