Trifluoroacetic acid → HCID 11494795, compound

HRID 1970934Notes

Reaction equation

HRID 1970934 reaction equation
C(O)(C(F)(F)F)=O.C(O[C:13](=[O:48])[CH2:14][N:15]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([C:24]([O:26][CH3:27])=[O:25])[CH:22]=2)[C:17]([CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)=[C:16]1[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[NH:40]C(OC(C)(C)C)=O)(C)(C)C.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1.O>[CH:28]1([C:17]2[C:18]3[CH:19]=[CH:20][C:21]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][C:23]=3[N:15]3[C:16]=2[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[NH:40][C:13](=[O:48])[CH2:14]3)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 58107384HCID 58107384, compound

Product 1

HCID 11494795HCID 11494795, compoundYield 75,000%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

TFA (5 mL) was added to a solution of methyl 1-(2-tert-butoxy-2-oxoethyl)-2-(2-(tert-butoxycarbonylamino)phenyl)-3-cyclohexyl-1H-indole-6-carboxylate (5.6 g, 10 mmol) in toluene (90 mL) and heated at 100° C. for 1 h. The reaction mixture was allowed to cool and then was carefully poured into a solution of NaHCO3 (10 g) in H2O (200 mL) while stirring. The resulting white precipitate was collected by filtration, flushed with water and EtOAc and dried under N2 to yield methyl 13-cyclohexyl-5H-indolo[1,2-d][1,4]benzodiazepine-6(7H)-one-10-carboxylate (2.9 g, 7.5 mol, 75%) as white solid. LCMS: m/e 389 (M+H)+, ret time 2.22 min.

Workup

  1. temperatureto cool
  2. filtrationThe resulting white precipitate was collected by filtration
  3. customflushed with water and EtOAc
  4. customdried under N2

Sources & evidence

ORD record
ord-ec61881c5d694106b9034c604bcc165d
Source dataset
uspto-grants-2013_04
Patent number
US08431568B2

Reaction notes

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