Trifluoroacetic acid → HCID 86708278, compound

HRID 534239Notes

Reaction equation

HRID 534239 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]([N:5]([CH2:15][C@H:16]1[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17]1)[C@@H:6]1[CH2:8][C@H:7]1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:4].C(O)(C(F)(F)F)=O>ClCCl>[F:29][C:2]([F:1])([F:28])[C:3]([N:5]([C@@H:6]1[CH2:8][C@H:7]1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:15][C@H:16]1[CH2:20][CH2:19][NH:18][CH2:17]1)=[O:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86708279HCID 86708279, compound

Product 1

HCID 86708278HCID 86708278, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-tert-butyl 3-((2,2,2-trifluoro-N-((1R,2S)-2-phenylcyclopropyl)acetamido) methyl)pyrrolidine-1-carboxylate (1.28 g, 3.10 mmol) in dichloromethane (DCM) (12 mL) was added TFA (3 ml, 38.9 mmol), and the mixture was stirred at room temperature for 3 h. The mixture was concentrated and the residue was treated with saturated NaHCO3 solution and extracted with DCM (3×). The extract was dried (Na2SO4) and concentrated. The residue was dried under vacuum to give 950 mg of product as pale yellow oil.

Workup

  1. concentrationThe mixture was concentrated
  2. additionthe residue was treated with saturated NaHCO3 solution
  3. extractionextracted with DCM (3×)
  4. dry with materialThe extract was dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was dried under vacuum

Sources & evidence

ORD record
ord-32337bde0e1f48839cafe2cdad42814c
Source dataset
uspto-grants-2014_10
Patent number
US08853408B2

Reaction notes

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