Trifluoroacetic acid → HCID 67235165, compound

HRID 1748304Notes

Reaction equation

HRID 1748304 reaction equation
C(O)(C(F)(F)F)=O.C(OC([NH:15][CH2:16][C:17]1([CH2:23][N:24]2[C:32]3[C:27](=[CH:28][CH:29]=[C:30]([C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH:31]=3)[CH:26]=[C:25]2[C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)=O)(C)(C)C>C(Cl)Cl>[NH2:15][CH2:16][C:17]1([CH2:23][N:24]2[C:32]3[C:27](=[CH:28][CH:29]=[C:30]([C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH:31]=3)[CH:26]=[C:25]2[C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH2:18][CH2:19][O:20][CH2:21][CH2:22]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67237067HCID 67237067, compound

Product 1

HCID 67235165HCID 67235165, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (60 mL) is added to a solution of crude diethyl 1-[(4-{[(tert-butoxycarbonyl)amino]methyl}tetrahydro-2H-pyran-4-yl)methyl]-1H-indole-2,6-dicarboxylate from the preceding step in CH2Cl2 (400 mL). The reaction mixture is stirred at room temperature for 2 h. Then the solvent is removed under vacuum and the residue is dissolved in EtOAc (300 mL) and washed with saturated NaHCO3 solution until the pH is about 7. The aqueous layer is separated and it is extracted with EtOAc (100 mL). The organic layers are combined, dried over Na2SO4 and concentrated to afford the crude title compound which is used in the next step without purification.

Workup

  1. customThen the solvent is removed under vacuum
  2. dissolutionthe residue is dissolved in EtOAc (300 mL)
  3. washwashed with saturated NaHCO3 solution until the pH is about 7
  4. customThe aqueous layer is separated
  5. extractionit is extracted with EtOAc (100 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e27fdfecd98247fc981fe365b1915a1d
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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