Trifluoroacetic acid → Methyl 3-bromo-6-(2,2-dimethylpropionylamino)-2-(2-pyrrolidin-2-yl-ethyl)benzoate

HRID 715969Notes

Reaction equation

HRID 715969 reaction equation
FC(F)(F)C(O)=O.[Br:8][C:9]1[C:14]([CH2:15][CH2:16][CH:17]2[CH2:21][CH2:20][CH2:19][N:18]2C(OC(C)(C)C)=O)=[C:13]([C:29]([O:31][CH3:32])=[O:30])[C:12]([NH:33][C:34](=[O:39])[C:35]([CH3:38])([CH3:37])[CH3:36])=[CH:11][CH:10]=1>C(Cl)Cl>[Br:8][C:9]1[C:14]([CH2:15][CH2:16][CH:17]2[CH2:21][CH2:20][CH2:19][NH:18]2)=[C:13]([C:12]([NH:33][C:34](=[O:39])[C:35]([CH3:37])([CH3:38])[CH3:36])=[CH:11][CH:10]=1)[C:29]([O:31][CH3:32])=[O:30]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70982387Tert-butyl 2-{2-[6-bromo-3-(2,2-dimethylpropionylamino)-2-methoxycarbonylphenyl]-ethyl}-pyrrolidine-1-carboxylate2×

Product 1

HCID 70982675Methyl 3-bromo-6-(2,2-dimethylpropionylamino)-2-(2-pyrrolidin-2-yl-ethyl)benzoateYield 100.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (15 mL) was added to a solution of tert-butyl 2-{2-[6-bromo-3-(2,2-dimethylpropionylamino)-2-methoxycarbonylphenyl]-ethyl}-pyrrolidine-1-carboxylate (Intermediate 36, 2.54 g) in DCM (15 mL) and the mixture was left to stand at room temperature for 30 minutes. The resultant solution was concentrated in vacuo and the residue was partitioned between ethyl acetate and potassium carbonate solution. The organic layer was dried (Na2SO4) and filtered and the filtrate was concentrated in vacuo to give methyl 3-bromo-6-(2,2-dimethylpropionylamino)-2-(2-pyrrolidin-2-yl-ethyl)benzoate (2.05 g) as a white foam.

Workup

  1. waitthe mixture was left
  2. concentrationThe resultant solution was concentrated in vacuo
  3. customthe residue was partitioned between ethyl acetate and potassium carbonate solution
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-1e5ba14e7ac04c6eaead59af8e7f7eee
Source dataset
uspto-grants-2015_11
Patent number
US09187494B2

Reaction notes

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