Trifluoroacetic acid → HCID 67234992, compound

HRID 1748280Notes

Reaction equation

HRID 1748280 reaction equation
C(OC([NH:8][CH2:9][CH2:10][C@@H:11]([N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:20]=2)[CH:15]=[C:14]1[C:27](OCC)=[O:28])[CH3:12])=O)(C)(C)C.C(O)(C(F)(F)F)=O.C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>C(Cl)Cl.C(O)C>[CH3:12][C@@H:11]1[N:13]2[C:21]3[CH:20]=[C:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:18]=[CH:17][C:16]=3[CH:15]=[C:14]2[C:27](=[O:28])[NH:8][CH2:9][CH2:10]1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 672355501H-Indole-2,6-dicarboxylic acid, 1-[(1S)-3-[[(1,1-dimethylethoxy)carbonyl]amino]-1-methylpropyl]-, 2,6-diethyl ester

Product 1

HCID 67234992HCID 67234992, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of diethyl 1-{(2S)-4-[(tert-butoxycarbonyl)amino]butan-2-yl}-1H-indole-2,6-dicarboxylate (891 mg, 2.1 mmol) in CH2Cl2 (4 mL) is added TFA (3 mL). The mixture is stirred at room temperature for 1 h then the solvent is evaporated. To a solution of the residue in ethanol (10 mL) is added K2CO3 (854 mg, 6.2 mmol). The reaction mixture is refluxed for 4 h with vigorous stifling. EtOAc is added and the organic layer is washed with water, brine, dried (MgSO4) and concentrated to afford crude compound which is purified by flash column chromatography using EtOAc in hexanes then methanol in CH2Cl2 to afford the title compound (269 mg, 46%).

Workup

  1. customthe solvent is evaporated
  2. temperatureThe reaction mixture is refluxed for 4 h with vigorous stifling
  3. washthe organic layer is washed with water, brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customto afford crude compound which
  7. customis purified by flash column chromatography

Sources & evidence

ORD record
ord-bac733a44370436a825fa64c10f3c4ff
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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