(S)-2-((tert)-Butoxycarbonyl)amino)butanoic acid → HCID 86722024, compound

HRID 525004Notes

Reaction equation

HRID 525004 reaction equation
[NH2:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[C:7]([NH:9][C:10]1[CH:15]=[C:14]([F:16])[CH:13]=[C:12]([F:17])[CH:11]=1)=[O:8].[C:18]([O:22][C:23]([NH:25][C@@H:26]([CH2:30]C)[C:27](O)=[O:28])=[O:24])([CH3:21])([CH3:20])[CH3:19]>C1COCC1.C(OCC)(=O)C.C(OC(C)C)(C)C>[F:17][C:12]1[CH:11]=[C:10]([NH:9][C:7]([C:3]2[N:2]([NH:1][C:27](=[O:28])[C@@H:26]([NH:25][C:23](=[O:24])[O:22][C:18]([CH3:20])([CH3:19])[CH3:21])[CH3:30])[CH:6]=[CH:5][N:4]=2)=[O:8])[CH:15]=[C:14]([F:16])[CH:13]=1

Participants

6

Reactant 2

HCID 2755934(S)-2-((tert)-Butoxycarbonyl)amino)butanoic acidHCID 86722025HCID 86722025, compound

Product 1

HCID 86722024HCID 86722024, compoundYield 59.7%

Reagents, catalysts & solvents 3

HCID 7914Diisopropyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
55 °C

Procedure

1.60 g (6.18 mmol) of 1-amino-N-(3,5-difluorophenyl)-1H-imidazole-2-carboxamide, 1.64 g (8.65 mmol) of (S)-2-(tert-butoxycarbonylamino)butanoic acid and 1.34 g (8.65 mmol) of EDCHCl were dissolved in 45 mL of THF and stirred at 55° C. overnight and at room temperature for 2 days. Then the solvent was evaporated and the crude residue was taken up in ethyl acetate and washed with brine. The organic layer was dried over magnesium sulphate, filtered and the solvent was evaporated. The solid obtained was redissolved in the minimum amount of ethyl acetate and diisopropylether was added until a solid precipitated, which was filtered to furnish 1.51 g (57% yield) of the title compound.

Workup

  1. customThen the solvent was evaporated
  2. washwashed with brine
  3. dry with materialThe organic layer was dried over magnesium sulphate
  4. filtrationfiltered
  5. customthe solvent was evaporated
  6. customThe solid obtained
  7. additionwas added until a solid
  8. customprecipitated
  9. filtrationwhich was filtered

Sources & evidence

ORD record
ord-37171a4adfef4076abf254a03be6212d
Source dataset
uspto-grants-2016_05
Patent number
US09340547B2

Reaction notes

Loading…