Trifluoroacetic acid → HCID 18713524, compound

HRID 279227Notes

Reaction equation

HRID 279227 reaction equation
C(OC([CH:8]([NH2:44])[CH2:9][CH2:10][N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][C:18]=2[C:20]([N:22]2[CH2:26][C@@H:25]([CH:27]3[CH2:29][CH2:28]3)[C@H:24]([CH2:30][N:31]3[CH2:36][CH2:35][CH:34]([C:37]4[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=4)[CH2:33][CH2:32]3)[CH2:23]2)=[O:21])[CH:13]=[CH:12]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>ClC(Cl)C.C1(C)C=CC=CC=1>[NH2:44][CH2:8][CH2:9][CH2:10][N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][C:18]=2[C:20]([N:22]2[CH2:26][C@@H:25]([CH:27]3[CH2:29][CH2:28]3)[C@H:24]([CH2:30][N:31]3[CH2:36][CH2:35][CH:34]([C:37]4[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=4)[CH2:33][CH2:32]3)[CH2:23]2)=[O:21])[CH:13]=[CH:12]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86757902HCID 86757902, compound

Product 1

HCID 18713524HCID 18713524, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 0.1 g (0.16 mmol) of 1-(N-(3-t-butoxycarbonyl aminopropyl)-7-indolecarbonyl)-3-(R)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(S)-(cyclopropyl)pyrrolidine in 2 mL of CH2C2 was added 0.3 mL of a 1M solution of TFA in dichloroethane and the reaction mixture was stirred at rt for 24 h. The reaction mixture was then diluted with toluene and concentrated. The residue was purified by chromatography (silica, CHCl3: MeOH: NH3, 90:10:1) to give 0.07 g of the title compound. Mass Spectrum (EI) m/e 503 (M+1).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by chromatography (silica, CHCl3: MeOH: NH3, 90:10:1)

Sources & evidence

ORD record
ord-5b4da2653d104b7a9478088e9435c5b6
Source dataset
uspto-grants-2002_03
Patent number
US06362201B1

Reaction notes

Loading…