Ammonia → HCID 178440691, compound

HRID 1424174Notes

Reaction equation

HRID 1424174 reaction equation
[NH2:1][C@H:2]([C:16]1[NH:20][C:19]2[CH:21]=[CH:22][C:23]([C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:24][C:18]=2[N:17]=1)[C:3]([CH3:15])([CH3:14])[C:4]([O:6]CC1C=CC=CC=1)=O.[NH3:29]>C1COCC1>[NH2:1][C@H:2]([C:16]1[NH:20][C:19]2[CH:21]=[CH:22][C:23]([C:25]([CH3:28])([CH3:26])[CH3:27])=[CH:24][C:18]=2[N:17]=1)[C:3]([CH3:14])([CH3:15])[C:4]([NH2:29])=[O:6]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 178440692HCID 178440692, compound

Product 1

HCID 178440691HCID 178440691, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzyl (3S)-3-amino-3-(5-tert-butyl-1H-benzimidazol-2-yl)-2,2-dimethylpropanoate (Preparation 13, 150 mg, 0.312 mmol) in THF (10 mL) was added freshly condensed liquid NH3 (20 mL) at −78° C. and the reaction was stirred at room temperature for 24 hours. The reaction mixture was evaporated and purified by preparative TLC eluting with 70% EtOAc in petroleum ether. The residue was dissolved in dioxane (6 mL), cooled to 0° C. and treated with 2N HCl in dioxane (4 mL). The reaction was stirred at room temperature for 4 hours before concentrating in vacuo. The residue was purified through an SCX cartridge to afford the title compound (25 mg, 30%).

Workup

  1. customThe reaction mixture was evaporated
  2. custompurified by preparative TLC
  3. washeluting with 70% EtOAc in petroleum ether
  4. dissolutionThe residue was dissolved in dioxane (6 mL)
  5. temperaturecooled to 0° C.
  6. additiontreated with 2N HCl in dioxane (4 mL)
  7. stirringThe reaction was stirred at room temperature for 4 hours
  8. concentrationbefore concentrating in vacuo
  9. customThe residue was purified through an SCX cartridge

Sources & evidence

ORD record
ord-03c8dd51c62d451fbc53da133a65265c
Source dataset
uspto-grants-2015_01
Patent number
US08927587B2

Reaction notes

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