Trifluoroacetic acid → HCID 67236001, compound

HRID 1748275Notes

Reaction equation

HRID 1748275 reaction equation
C(OC([C:6]1[N:7]([C@H:20]([CH3:31])[CH2:21][CH2:22][NH:23][C:24](OC(C)(C)C)=[O:25])[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[C:10]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:9]=2)=O)C.C(O)(C(F)(F)F)=O.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.C(O)C>[CH3:31][C@H:20]1[N:7]2[C:8]3[CH:9]=[C:10]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:11]=[CH:12][C:13]=3[CH:14]=[C:6]2[C:24](=[O:25])[NH:23][CH2:22][CH2:21]1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 67235300HCID 67235300, compound

Product 1

HCID 67236001HCID 67236001, compoundYield 91.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-((R)-3-tert-butoxycarbonylamino-1-methyl-propyl)-1H-indole-2,6-dicarboxylic acid diethyl ester (6.0 g, crude) in CH2Cl2 (27 mL) is added TFA (18.1 mL). The reaction mixture is stirred for 1 hour and the solvent is removed under vacuum. To a solution of the residue in ethanol (90 mL) is added K2CO3 (4.6 g, 33.3 mmol) and the reaction mixture is heated to reflux for 2 hours. The cooled reaction mixture is poured into ice water and extracted with EtOAc. The combined extracts are washed with water, brine, dried (Na2SO4) and concentrated to afford the title compound (3.65 g, crude) as a brown oil.

Workup

  1. customthe solvent is removed under vacuum
  2. temperaturethe reaction mixture is heated
  3. temperatureto reflux for 2 hours
  4. customThe cooled reaction mixture
  5. extractionextracted with EtOAc
  6. washThe combined extracts are washed with water, brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-6f51b5a0795241d28cda8dfc65021245
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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