Sodium Hydroxide → 2-Tert-butoxycarbonylamino-4-1,2,3-triazol-2-yl-butyric acid

HRID 1040505Notes

Reaction equation

HRID 1040505 reaction equation
C[O:2][C:3](=[O:20])[CH:4]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:5][CH2:6][N:7]1[N:11]=[CH:10][CH:9]=[N:8]1.[OH-].[Na+]>CO>[C:16]([O:15][C:13]([NH:12][CH:4]([CH2:5][CH2:6][N:7]1[N:8]=[CH:9][CH:10]=[N:11]1)[C:3]([OH:20])=[O:2])=[O:14])([CH3:19])([CH3:17])[CH3:18]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 584311562-Tert-butoxycarbonylamino-4-1,2,3-triazol-2-yl-butyric acid methyl ester

Product 1

HCID 668978472-Tert-butoxycarbonylamino-4-1,2,3-triazol-2-yl-butyric acidYield 97.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 0.50 g (1.6 mmol) of 2-tert-butoxycarbonylamino-4-1,2,3-triazol-2-yl-butyric acid methyl ester in 1.0 mL of MeOH and 3.0 mL (9.0 mmol) of 3M aq. NaOH is stirred at 80° C. for 60 min The mixture was cooled to rt and washed with EtOAc (1×10 mL). After adjusting the pH to 4 with 3M HCl, the mixture is extracted with EtOAc (3×) and the extracts are washed with brine, then dried with Na2SO4, filtered, and concentrated to provide 0.42 g (87%) of 2-tert-butoxycarbonylamino-4-1,2,3-triazol-2-yl-butyric acid as a white solid.

Workup

  1. temperaturewas cooled to rt
  2. washwashed with EtOAc (1×10 mL)
  3. extractionthe mixture is extracted with EtOAc (3×)
  4. washthe extracts are washed with brine
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-85724ea07a394ad497a7c0d0b0caab79
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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