Water → Tert-butyl[2-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-ethyl]-carbamate

HRID 1804568Notes

Reaction equation

HRID 1804568 reaction equation
[OH:1][NH:2][C:3](=[NH:7])[CH:4]([CH3:6])[CH3:5].[H-].[Na+].[C:10]([O:14][C:15]([NH:17][CH2:18][CH2:19][C:20](OC)=O)=[O:16])([CH3:13])([CH3:12])[CH3:11].O>CN(C)C=O>[CH:4]([C:3]1[N:7]=[C:20]([CH2:19][CH2:18][NH:17][C:15](=[O:16])[O:14][C:10]([CH3:13])([CH3:12])[CH3:11])[O:1][N:2]=1)([CH3:6])[CH3:5]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 11687095Methyl 3-(((tert-butoxy)carbonyl)amino)propanoateHCID 178449908HCID 178449908, compound

Product 1

HCID 57637051Tert-butyl[2-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-ethyl]-carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
50 °C

Procedure

2.20 g (21.54 mmol) N-hydroxy-isobutyramidine are placed in 10 ml dimethylformamide and molecular sieve. 0.948 g (23.69 mmol) sodium hydride (60% in mineral oil) are added. The mixture is stirred for 0.1 hours at 50° C., then 6.20 g (30.51 mmol) methyl 3-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, the aqueous phase is extracted with ethyl acetate, the combined organic phases are 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. extractionthe aqueous phase is extracted with ethyl acetate
  6. customthe combined organic phases are evaporated down
  7. customThe residue is purified by chromatography

Sources & evidence

ORD record
ord-91816947d6704168a1593d982a18d26f
Source dataset
uspto-grants-2013_01
Patent number
US08354418B2

Reaction notes

Loading…