Hydrochloric Acid → 2-Tert-butoxycarbonylamino-3-(2-hydroxy-4-methoxy-phenyl)propanoic acid

HRID 540413Notes

Reaction equation

HRID 540413 reaction equation
[OH-].[Na+].[C:3]([O:7][C:8]([NH:10][CH:11]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=1[OH:25])[C:12]([O:14]C)=[O:13])=[O:9])([CH3:6])([CH3:5])[CH3:4].Cl>O1CCCC1>[C:3]([O:7][C:8]([NH:10][CH:11]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=1[OH:25])[C:12]([OH:14])=[O:13])=[O:9])([CH3:5])([CH3:6])[CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 397418Methyl 2-tert-butoxycarbonylamino-3-(2-hydroxy-4-methoxyphenyl)-propanoate

Product 1

HCID 669881482-Tert-butoxycarbonylamino-3-(2-hydroxy-4-methoxy-phenyl)propanoic acidYield 101.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5 ml of a 1N aqueous solution of sodium hydroxide are added to a solution of 850 mg (2.6 mmol) of methyl 2-tert-butoxycarbonylamino-3-(2-hydroxy-4-methoxyphenyl)-propanoate in 10 ml of tetrahydrofuran. The reaction medium is stirred for 4 hours at ambient temperature and then a 1N aqueous solution of hydrochloric acid is added until the pH is 1, and the medium is extracted with dichloromethane. The organic phase is dried over magnesium sulphate, filtered and evaporated. 820 mg of 2-tert-butoxycarbonylamino-3-(2-hydroxy-4-methoxy-phenyl)propanoic acid are obtained in the form of a beige powder with a quantitative yield.

Workup

  1. extractionthe medium is extracted with dichloromethane
  2. dry with materialThe organic phase is dried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-807e9f4bda234db3b1d8b8f9f36c4a67
Source dataset
uspto-grants-2014_10
Patent number
US08871187B2

Reaction notes

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