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

HRID 2110937Notes

Reaction equation

HRID 2110937 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>[C:10]([O:14][C:15](=[O:16])[NH:17][CH2:18][CH2:19][C:20]1[O:1][N:2]=[C:3]([CH:4]([CH3:6])[CH3:5])[N:7]=1)([CH3:13])([CH3:12])[CH3:11]

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, 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 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. extractionthe aqueous phase is extracted with ethyl acetate
  6. customthe combined organic phase is evaporated down
  7. customThe residue is purified by chromatography

Sources & evidence

ORD record
ord-166651a1801948b09088fc8f353fbee6
Source dataset
uspto-grants-2009_04
Patent number
US07517995B2

Reaction notes

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