1,1'-Carbonyldiimidazole → Tert-butyl (1-(3-methyl-1,2,4-oxadiazol-5-yl)cyclopropyl)carbamate

HRID 2038787Notes

Reaction equation

HRID 2038787 reaction equation
[C:1]([NH:8][C:9]1([C:12]([OH:14])=O)[CH2:11][CH2:10]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N1C=CN=C1)(N1C=CN=C1)=O.O[NH:28][C:29](=[NH:31])[CH3:30]>CN(C=O)C.O>[C:4]([O:3][C:1](=[O:2])[NH:8][C:9]1([C:12]2[O:14][N:31]=[C:29]([CH3:30])[N:28]=2)[CH2:10][CH2:11]1)([CH3:5])([CH3:6])[CH3:7]

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 6883961-((tert-Butoxycarbonyl)amino)cyclopropanecarboxylic acidHCID 178465666HCID 178465666, compound

Product 1

HCID 56965655Tert-butyl (1-(3-methyl-1,2,4-oxadiazol-5-yl)cyclopropyl)carbamateYield 87.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of N-boc-amino-cyclopropanecarboxylic acid (1.01 g, 5.00 mmol) in 2 mL of DMF was added carbonyldiimidazole (0.812 g, 5.01 mmol). This reaction mixture was stirred at room temperature for 6 h. N-Hydroxy-acetamidine (0.374 g, 5.05 mmol) was added. This reaction mixture was stirred at room temperature for 2 h then heated at 100° C. for 16 h. After cooling to room temperature, the reaction mixture was diluted with water. The resultant precipitate was collected by filtration, washed with acetonitrile and water and air-dried to give 1.05 g of [1-(3-methyl-1,2,4-oxadiazol-5-yl)-cyclopropyl]-carbamic acid tert-butyl ester as a white solid, m/z 240 [M+1]+.

Workup

  1. stirringThis reaction mixture was stirred at room temperature for 2 h
  2. temperaturethen heated at 100° C. for 16 h
  3. temperatureAfter cooling to room temperature
  4. filtrationThe resultant precipitate was collected by filtration
  5. washwashed with acetonitrile and water
  6. customair-dried

Sources & evidence

ORD record
ord-77c122b19b664064b52851fe959c7ba1
Source dataset
uspto-grants-2013_11
Patent number
US08575360B2

Reaction notes

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