Trifluoroacetic acid → HCID 18348855, compound

HRID 2268656Notes

Reaction equation

HRID 2268656 reaction equation
C(OC(=O)[N:7]([CH2:14][CH2:15][O:16][C:17]1[CH:22]=[C:21]([C:23](=[O:43])[N:24]([CH2:32][CH2:33][O:34][CH2:35][CH:36]2[CH2:40][O:39]C(C)(C)[O:37]2)[C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[CH:20]=[C:19]([Cl:44])[CH:18]=1)[C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[ClH:44].[Cl:44][C:19]1[CH:20]=[C:21]([CH:22]=[C:17]([O:16][CH2:15][CH2:14][NH:7][C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[CH:18]=1)[C:23]([N:24]([CH2:32][CH2:33][O:34][CH2:35][CH:36]([OH:37])[CH2:40][OH:39])[C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1)=[O:43]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54432608HCID 54432608, compound

Product 1

HCID 18348855HCID 18348855, compoundYield 124.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (2-{3-chloro-5-[[2-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-ethyl]-(4-fluoro-phenyl)-carbamoyl]-phenoxy}-ethyl)-pyridin-4-yl-carbamic acid tert-butyl ester (0.042 g) in mixture of trifluoroacetic acid (1 ml) and dichloromethane (1 ml) was stored at room temperature for 3 h and then the solvent removed under reduced pressure. The residue was dissolved in a mixture of acetonitrile (2 ml) amd 2M aqueous hydrochloric acid (0.5 ml) and subjected to preparative hplc to give title compound (0.022 g) as a colourless gum by concentration of the required fraction under reduced pressure and drying by repetitive addition of acetonitrile and concentration under reduced pressure.

Workup

  1. customthe solvent removed under reduced pressure
  2. dissolutionThe residue was dissolved in a mixture of acetonitrile (2 ml)

Sources & evidence

ORD record
ord-fb36a5a136e24cda8de839f5e3bb9e02
Source dataset
uspto-grants-2001_12
Patent number
US06326386B1

Reaction notes

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