Trifluoroacetic acid → HCID 59254366, compound

HRID 639066Notes

Reaction equation

HRID 639066 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]([NH:5][CH2:6][C@@H:7]1[CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8]1)=[O:4].C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:20][C:2]([F:1])([F:19])[C:3]([NH:5][CH2:6][C@@H:7]1[CH2:11][CH2:10][NH:9][CH2:8]1)=[O:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59026224HCID 59026224, compound

Product 1

HCID 59254366HCID 59254366, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1,1-dimethylethyl(3S)-3{[(trifluoroacetyl)amino]methyl}-1-pyrrolidinecarboxylate (2.96 g, 10.0 mmole), in CH2Cl2 (50 mL) at RT was added TFA (25 mL). After 2 h, the reaction contents were concentrated under vacuum. The remaining residue was dissolved in (CHCl3/i-PrOH, 10:1) and washed with saturated aqueous NaHCO3. The organic phase was separated and dried over Na2SO4. Concentration under vacuum afforded the title compound (1.86 g, 95%) as a yellow oil: LC-MS (ES) m/e 197 (M+H)+.

Workup

  1. customthe reaction contents
  2. concentrationwere concentrated under vacuum
  3. dissolutionThe remaining residue was dissolved in (CHCl3/i-PrOH, 10:1)
  4. washwashed with saturated aqueous NaHCO3
  5. customThe organic phase was separated
  6. dry with materialdried over Na2SO4
  7. concentrationConcentration under vacuum

Sources & evidence

ORD record
ord-1167713177f94c1e83d3300370114430
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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