Trifluoroacetic acid → HCID 67235121, compound

HRID 1748311Notes

Reaction equation

HRID 1748311 reaction equation
C(OC([NH:8][CH:9]([CH3:31])[CH2:10][CH2:11][N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:19]=2)[CH:14]=[C:13]1[C:26](OCC)=[O:27])=O)(C)(C)C.N1C2C(=CC=C(C(OCC)=O)C=2)C=C1C(OCC)=O.C(O)(C(F)(F)F)=O.C([O-])([O-])=O.[K+].[K+].C(N(CC)CC)C>C(Cl)Cl.C(O)C.O>[CH3:31][CH:9]1[CH2:10][CH2:11][N:12]2[C:20]3[CH:19]=[C:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:17]=[CH:16][C:15]=3[CH:14]=[C:13]2[C:26](=[O:27])[NH:8]1

Participants

9

Reactant 5

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 44754779Diethyl 1H-indole-2,6-dicarboxylateHCID 67235695HCID 67235695, compound

Product 1

HCID 67235121HCID 67235121, compoundYield 15%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of diethyl 1-{3-[(tert-butoxycarbonyl)amino]butyl}-1H-indole-2,6-dicarboxylate and diethyl 1H-indole-2,6-dicarboxylate (600 mg) in CH2Cl2 (10 mL) is added TFA (5 mL). The reaction mixture is stirred for 2 h at room temperature. The solvent is evaporated and the residue dried in vacuo. To a solution of the residue in ethanol (10 mL) is added K2CO3 (500 mg, 3.6 mmol) and triethylamine (0.02 mL, 0.14 mmol). The reaction mixture is heated to 80° C. for 36 h. The mixture is diluted with water (10 mL) and is extracted with EtOAc. The organic layers are dried (Na2SO4) and concentrated and the residue is purified by flash column chromatography using EtOAc in heptane to afford the title compound (120 mg, 15% for 3 steps).

Workup

  1. customThe solvent is evaporated
  2. customthe residue dried in vacuo
  3. temperatureThe reaction mixture is heated to 80° C. for 36 h
  4. extractionis extracted with EtOAc
  5. dry with materialThe organic layers are dried (Na2SO4)
  6. concentrationconcentrated
  7. customthe residue is purified by flash column chromatography

Sources & evidence

ORD record
ord-acf8ffb44e544722b0f5b570052ef0e5
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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