Trifluoroacetic acid → HCID 67235374, compound

HRID 1748296Notes

Reaction equation

HRID 1748296 reaction equation
C(O)(C(F)(F)F)=O.C(OC([NH:15][CH2:16][C:17]1([CH2:20][N:21]2[C:29]3[C:24](=[CH:25][CH:26]=[C:27]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH:28]=3)[CH:23]=[C:22]2[C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH2:19][CH2:18]1)=O)(C)(C)C>C(Cl)Cl>[NH2:15][CH2:16][C:17]1([CH2:20][N:21]2[C:29]3[C:24](=[CH:25][CH:26]=[C:27]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH:28]=3)[CH:23]=[C:22]2[C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH2:18][CH2:19]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67234930HCID 67234930, compound

Product 1

HCID 67235374HCID 67235374, compoundYield 107.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (120 mL) is added to a solution of crude diethyl 1-[(1-{[(tert-butoxycarbonyl)amino]methyl}cyclopropyl)methyl]-1H-indole-2,6-dicarboxylate (36 g, 81 mmol) in CH2Cl2 (700 mL) at room temperature. The reaction mixture is stirred for 2 h and the solvent is evaporated. The residue is dissolved in EtOAc (600 mL) and is washed with saturated NaHCO3 until the pH is about 7. The aqueous layer is extracted with EtOAc (2×100 mL) and the combined organic layers are dried (Na2SO4), and concentrated to afford the title compound (30 g, >99%) as a light yellow colored oil which is used in the next step without purification.

Workup

  1. customthe solvent is evaporated
  2. dissolutionThe residue is dissolved in EtOAc (600 mL)
  3. washis washed with saturated NaHCO3 until the pH is about 7
  4. extractionThe aqueous layer is extracted with EtOAc (2×100 mL)
  5. dry with materialthe combined organic layers are dried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-31231b7f7d5b45ebaa8187cc25c419de
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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