Trifluoroacetic acid → HCID 68889281, compound

HRID 853046Notes

Reaction equation

HRID 853046 reaction equation
C(OC([C:6]1[N:7]([C@H:19]([CH3:29])[CH2:20][NH:21][C:22]([O:24]C(C)(C)C)=O)[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[C:10]([C:15]([F:18])([F:17])[F:16])[CH:9]=2)=O)C.FC(F)(F)C(O)=O>ClCCl>[CH3:29][C@H:19]1[N:7]2[C:8]3[CH:9]=[C:10]([C:15]([F:18])([F:16])[F:17])[CH:11]=[CH:12][C:13]=3[CH:14]=[C:6]2[C:22](=[O:24])[NH:21][CH2:20]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69414220HCID 69414220, compound

Product 1

HCID 68889281HCID 68889281, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-1-(2-tert-Butoxycarbonylamino-1-methyl-ethyl)-6-trifluoromethyl-1H-indole-2-carboxylic acid ethyl ester (4.9 g, 12 mmol) was dissolved in dichloromethane (40 mL) and treated with trifluoroacetic acid (18.3 mL) at 0° C. After removal of the ice bath, the solution was stirred for 30 min, and evaporated under reduced pressure. The residue was dissolved in methanol (40 mL), then after addition of saturated sodium bicarbonate solution (90 mL) the mixture was stirred for 20 h at room temperature. Water (100 mL) was added and the mixture was extracted with dichloromethane (2×100 mL). The organic layer was separated, washed with brine, dried (MgSO4), and evaporated. Chromatography on silica gel with hexane/ethyl acetate (1:1) yielded the title compound as a white solid (2.9 g, 90%). M.p.: 201–204° C., EI-MS: m/e=268.2 (M+), αD20=+7.5

Workup

  1. customAfter removal of the ice bath
  2. customevaporated under reduced pressure
  3. dissolutionThe residue was dissolved in methanol (40 mL)
  4. additionafter addition of saturated sodium bicarbonate solution (90 mL) the mixture
  5. stirringwas stirred for 20 h at room temperature
  6. additionWater (100 mL) was added
  7. extractionthe mixture was extracted with dichloromethane (2×100 mL)
  8. customThe organic layer was separated
  9. washwashed with brine
  10. dry with materialdried (MgSO4)
  11. customevaporated

Sources & evidence

ORD record
ord-927e0516a34a4555b5fce1469bcd68cd
Source dataset
uspto-grants-2007_08
Patent number
US07253281B2

Reaction notes

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