1,1'-Carbonyldiimidazole → HCID 67391404, compound

HRID 1040433Notes

Reaction equation

HRID 1040433 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.[OH:27][CH:28]([CH3:34])[CH2:29][C:30]([NH:32]O)=[NH:31]>CN(C=O)C.O>[C:4]([O:3][C:1](=[O:2])[NH:8][C:9]1([C:12]2[O:14][N:32]=[C:30]([CH2:29][CH:28]([OH:27])[CH3:34])[N:31]=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 178467964HCID 178467964, compound

Product 1

HCID 67391404HCID 67391404, compoundYield 34.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of N-boc-amino-cyclopropanecarboxylic acid (500 mg, 2.49 mmol) in 2 mL of DMF at 0° C. was added carbonyldiimidazole (403 mg, 2.49 mmol). The reaction mixture was stirred at room temperature for 30 min, and 3,N-dihydroxy-butyramidine (480 mg, 4.06 mmol) was added as a solution in 2 mL of DMF. The pale yellow, faintly cloudy reaction mixture was stirred at room temperature for 30 min and then heated at 100° C. for 15 h. After cooling to room temperature, the reaction mixture was diluted with 15 mL of water and extracted with 50 mL of ethyl acetate. The organics were washed with 2×15 mL of water and 15 mL of brine, dried over Na2SO4, filtered, and concentrated. The crude was purified by flash chromatography on silica gel (0-8% MeOH/CH2Cl2) to afford 242 mg (34%) of {1-[3-(2-hydroxy-propyl)-1,2,4-oxadiazol-5-yl]-cyclopropyl}-carbamic acid tert-butyl ester as a pale yellow oil.

Workup

  1. customThe pale yellow, faintly cloudy reaction mixture
  2. stirringwas stirred at room temperature for 30 min
  3. temperatureheated at 100° C. for 15 h
  4. temperatureAfter cooling to room temperature
  5. extractionextracted with 50 mL of ethyl acetate
  6. washThe organics were washed with 2×15 mL of water and 15 mL of brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude was purified by flash chromatography on silica gel (0-8% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-c08663077dbc4d0e8fd844e261150197
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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