Trifluoroacetic acid → HCID 131719930, compound

HRID 1602715Notes

Reaction equation

HRID 1602715 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([NH:16][NH:17][C:18]([C:20]2[CH:34]=[CH:33][C:23]([O:24][CH2:25][C:26]([O:28]C(C)(C)C)=[O:27])=[C:22]([O:35][CH2:36][C:37]([O:39]C(C)(C)C)=[O:38])[CH:21]=2)=[O:19])=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C.[C:44]([OH:50])([C:46]([F:49])([F:48])[F:47])=[O:45]>ClCCl>[F:47][C:46]([F:49])([F:48])[C:44]([OH:50])=[O:45].[NH:8]1[CH2:13][CH2:12][CH:11]([C:14]([NH:16][NH:17][C:18]([C:20]2[CH:34]=[CH:33][C:23]([O:24][CH2:25][C:26]([OH:28])=[O:27])=[C:22]([O:35][CH2:36][C:37]([OH:39])=[O:38])[CH:21]=2)=[O:19])=[O:15])[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 19610507HCID 19610507, compound

Product 1

HCID 131719930HCID 131719930, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of t-butyl 4-[3-(1-t-butoxycarbonyl-piperidin-4-ylcarbonyl)-carbazoyl]-2-(t-butoxycarbonylmethoxy)phenoxyacetate (360 mg) and TFA (4 ml) in dichloromethane (8 ml) was stirred at ambient temperature for 5 hours. The solvent was removed by evaporation and the residue was triturated with ether to give the title compound as a solid; NMR Spectrum (d6 -DMSO) 1.68-2.02 (m, 4H), 2.55-2.68 (m, 1H), 2.85-3.05 (dt, 2H), 3.2-3.4 (br d, 2H), 4.74 (s, 2H), 4.78 (s, 2H), 6.97 (d, 1H), 7.4 (s, 1H), 7.47 (dd, 1H), 8.5 (br s, 2H), 9.9 (s, 1H), 10.2 (s, 1H); Mass Spectrum (+ve FAB, MeOH/NBA): 396 (M+H)+.

Workup

  1. customThe solvent was removed by evaporation
  2. customthe residue was triturated with ether

Sources & evidence

ORD record
ord-bbc85d1213b140059a8593a6b50f2a0e
Source dataset
uspto-grants-1999_11
Patent number
US05981531

Reaction notes

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