Trifluoroacetic acid → HCID 67193617, compound

HRID 515335Notes

Reaction equation

HRID 515335 reaction equation
FC(F)(F)C(O)=O.[CH:8]1([CH2:11][NH:12][C:13](=[O:38])[NH:14][C:15]2[CH:37]=[CH:36][C:18]([C:19]([N:21]([CH:23]3[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][CH2:24]3)[CH3:22])=[O:20])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1>ClCCl>[CH:8]1([CH2:11][NH:12][C:13](=[O:38])[NH:14][C:15]2[CH:37]=[CH:36][C:18]([C:19]([N:21]([CH3:22])[CH:23]3[CH2:24][CH2:25][NH:26][CH2:27][CH2:28]3)=[O:20])=[CH:17][CH:16]=2)[CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67191083HCID 67191083, compound

Product 1

HCID 67193617HCID 67193617, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,2,2-Trifluoroacetic acid (1.88 mL, 24.39 mmol) was added to a solution of tert-butyl 4-(4-(3-(cyclopropylmethyl)ureido)-N-methylbenzamido)piperidine-1-carboxylate (420 mg, 0.975 mmol) in dichloromethane (10 mL). The mixture was stirred at ambient temperature for 4 hours and then treated with strong cation exchange column chromatography to afford the title compound (300 mg). MS (ESI) m/z 331.1 [M+H]+

Workup

  1. additiontreated with strong cation exchange column chromatography

Sources & evidence

ORD record
ord-5c8fd0e5448c442391f51dfbc423ec6c
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

Loading…