Trifluoroacetic acid → HCID 67235090, compound

HRID 1748310Notes

Reaction equation

HRID 1748310 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][C:18]([CH2:30][N:31]2[C:39]3[C:34](=[CH:35][CH:36]=[C:37]([C:40]([O:42][CH2:43][CH3:44])=[O:41])[CH:38]=3)[CH:33]=[C:32]2C(OCC)=O)([CH2:21][NH:22][C:23]([O:25]C(C)(C)C)=O)[CH2:17][CH2:16]1)=O)(C)(C)C.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[O:25]=[C:23]1[C:32]2=[CH:33][C:34]3[CH:35]=[CH:36][C:37]([C:40]([O:42][CH2:43][CH3:44])=[O:41])=[CH:38][C:39]=3[N:31]2[CH2:30][C:18]2([CH2:17][CH2:16][NH:15][CH2:20][CH2:19]2)[CH2:21][NH:22]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 67235237HCID 67235237, compound

Product 1

HCID 67235090HCID 67235090, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (13.4 mL, 173.8 mmol) is added dropwise to the solution of diethyl 1-{[1-(tert-butoxycarbonyl)-4-{[(tert-butoxycarbonyl)amino]methyl}piperidin-4-yl]methyl}-1H-indole-2,6-dicarboxylate (17 g, 29.0 mmol) in CH2Cl2 (200 mL) at 0° C. The reaction mixture is stirred for 3 h at room temperature and then is basified with aqueous K2CO3 solution until the pH is 8. The aqueous layer is separated and extracted with CH2Cl2 (2×250 mL). The organic layers are combined, washed with brine, dried (Na2SO4) and concentrated. The crude material is recrystallized using diethyl ether to afford the title compound (6 g, 61%) as a white solid.

Workup

  1. customThe aqueous layer is separated
  2. extractionextracted with CH2Cl2 (2×250 mL)
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude material is recrystallized

Sources & evidence

ORD record
ord-d126d051e0d843499539cff15e58dbc7
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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