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

HRID 2110939Notes

Reaction equation

HRID 2110939 reaction equation
[OH:1][NH:2][C:3]([CH:5]1[CH2:7][CH2:6]1)=[NH:4].[H-].[Na+].[C:10]([O:14][C:15]([NH:17][CH2:18][CH2:19][C:20](OCC)=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:5]2[CH2:7][CH2:6]2)[N:4]=1)([CH3:13])([CH3:12])[CH3:11]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 15933116Ethyl 3-{[(tert-butoxy)carbonyl]amino}propanoateHCID 178513214HCID 178513214, compound

Product 1

HCID 57637077Tert-butyl[2-(3-cyclopropyl-[1,2,4]oxadiazol-5-yl)-ethyl]-carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
50 °C

Procedure

3.10 g (30.96 mmol) N-hydroxy-cyclopropanecarboxamidine are placed in 10 ml dimethylformamide and molecular sieve. 1.32 g (34.06 mmol) sodium hydride (60% in mineral oil) are added. The mixture is stirred for 0.1 hours at 50° C., then 7.40 g (34.06 mmol) ethyl 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-9f3f3e6ad548429590d893ba0dac2779
Source dataset
uspto-grants-2009_04
Patent number
US07517995B2

Reaction notes

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