Water → [2-(3-Ethyl-[1,2,4]oxadiazol-5-yl)-ethyl]-carbamic acid tert-butyl ester

HRID 1804566Notes

Reaction equation

HRID 1804566 reaction equation
[OH:1][NH:2][C:3](=[NH:6])[CH2:4][CH3:5].[H-].[Na+].CO[C:11](=O)[CH2:12][CH2:13][NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16].O>CN(C)C=O>[CH2:4]([C:3]1[N:6]=[C:11]([CH2:12][CH2:13][NH:14][C:15](=[O:16])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[O:1][N:2]=1)[CH3:5]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 11687095Methyl 3-(((tert-butoxy)carbonyl)amino)propanoateHCID 178458070HCID 178458070, compound

Product 1

HCID 57637085[2-(3-Ethyl-[1,2,4]oxadiazol-5-yl)-ethyl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
50 °C

Procedure

2.00 g (22.70 mmol) N-hydroxy-propionamidine are placed in 10 ml dimethylformamide and molecular sieve. 0.999 g (24.97 mmol) sodium hydride (60% in mineral oil) are added. The mixture is stirred for 0.1 hours at 50° C., then 5.00 g (24.60 mmol) methyl3-tert-butoxycarbonylamino-propionate in 20 ml dimethylformamide are added. The reaction mixture is stirred for 3 hours at 50° C. After cooling 15 ml of water are added, and the mixture is suction filtered through Celite. The 2 phases of the filtrate are separated and the organic phase is evaporated down. The residue is purified by chromatography.

Workup

  1. stirringThe reaction mixture is stirred for 3 hours at 50° C
  2. additionare added
  3. filtrationfiltered through Celite
  4. customThe 2 phases of the filtrate are separated
  5. customthe organic phase is evaporated down
  6. customThe residue is purified by chromatography

Sources & evidence

ORD record
ord-7029a097082f469d869a5b6c897b7f40
Source dataset
uspto-grants-2013_01
Patent number
US08354418B2

Reaction notes

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