Dimethylformamide → 2-Tert-butoxycarbonylamino-4-1,2,3-triazol-2-yl-butyric acid methyl ester

HRID 1040504Notes

Reaction equation

HRID 1040504 reaction equation
ClC1[NH:3][CH:4]=[CH:5][N:6]=1.[H-].[Na+].[CH3:9][O:10][C:11](=[O:24])[CH:12]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:14]Br.C[N:26](C=O)C>CCOC(C)=O>[CH3:9][O:10][C:11](=[O:24])[CH:12]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:14][N:26]1[N:3]=[CH:4][CH:5]=[N:6]1

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 27733282-chloro-1H-imidazoleHCID 6857808Methyl 4-bromo-2-(tert-butoxycarbonylamino)butanoate

Product 1

HCID 584311562-Tert-butoxycarbonylamino-4-1,2,3-triazol-2-yl-butyric acid methyl esterYield 78%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 0.87 g (8.4 mmol) of 2-chloroimidazole in 14 mL of DMF was added 0.40 g (10 mmol) of 60% NaH in mineral oil. After 20 min of stirring, 2.5 g (8.4 mmol) of 4-bromo-2-tert-butoxycarbonylamino-butyric acid methyl ester in 5 mL of DMF was added. The reaction mixture was heated to 80° C. for 1 h. The mixture was diluted with EtOAc (150 mL), washed with water, brine, dried over MgSO4, filtered, and concentrated. The residue was purified by flash chromatography (0-5% MeOH in CH2Cl2) to provide 2.1 g (78%) of 2-tert-butoxycarbonylamino-4-1,2,3-triazol-2-yl-butyric acid methyl ester.

Workup

  1. washwashed with water, brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (0-5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-ea4bce33fde64ba09b2357b934736a15
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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