Trifluoroacetic acid → HCID 67236248, compound

HRID 1748313Notes

Reaction equation

HRID 1748313 reaction equation
C(OC([NH:8][C:9]([CH3:32])([CH3:31])[CH2:10][CH2:11][N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([C:21]([O:23]CC)=[O:22])[CH:19]=2)[CH:14]=[C:13]1[C:26]([O:28]CC)=[O:27])=O)(C)(C)C.C(O)(C(F)(F)F)=O.C(N(CC)CC)C.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.C(O)(=O)C.O>[NH2:8][C:9]([CH3:32])([CH3:31])[CH2:10][CH2:11][N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([C:21]([OH:23])=[O:22])[CH:19]=2)[CH:14]=[C:13]1[C:26]([OH:28])=[O:27]

Participants

8

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 67235338HCID 67235338, compound

Product 1

HCID 67236248HCID 67236248, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To the mixture of the crude diethyl 1-{3-[(tert-butoxycarbonyl)amino-]-3-methylbutyl}-1H-indole-2,6-dicarboxylate from the preceding step in CH2Cl2 (3 mL) is added TFA (1.5 mL). The mixture is stirred at room temperature for 2 h. The solvent is evaporated and the residue dried in vacuo. To a solution of the residue in ethanol (8 mL). is added triethylamine (0.13 mL, 0.90 mmol) and K2CO3 (124 mg, 0.90 mmol). The mixture is heated at 80° C. for 2 h and at 100° C. for 64 h. Water (20 mL) and acetic acid (1 mL) are added and the mixture is extracted with EtOAc. The organic layers are dried (Na2SO2) and concentrated to afford the title compound which is used in the next step without purification.

Workup

  1. customThe solvent is evaporated
  2. customthe residue dried in vacuo
  3. temperatureThe mixture is heated at 80° C. for 2 h and at 100° C. for 64 h
  4. extractionthe mixture is extracted with EtOAc
  5. dry with materialThe organic layers are dried (Na2SO2)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-80ae1f95fd2e491ab719a72a52e359d0
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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