Trifluoroacetic acid → HCID 23501852, compound

HRID 2228538Notes

Reaction equation

HRID 2228538 reaction equation
C(OC([NH:8][CH2:9][CH2:10][O:11][C:12](=[O:52])[CH2:13][CH2:14][NH:15][C:16]([CH:18]1[CH2:27][CH2:26][C:25]2[C:20](=[C:21]([CH2:49][CH2:50][CH3:51])[C:22]([O:28][CH2:29][CH2:30][CH2:31][O:32][C:33]3[C:38]([CH2:39][CH3:40])=[CH:37][C:36]([C:41]4[CH:46]=[CH:45][C:44]([F:47])=[CH:43][CH:42]=4)=[C:35]([OH:48])[CH:34]=3)=[CH:23][CH:24]=2)[O:19]1)=[O:17])=O)(C)(C)C.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>ClCCl>[NH2:8][CH2:9][CH2:10][O:11][C:12](=[O:52])[CH2:13][CH2:14][NH:15][C:16]([CH:18]1[CH2:27][CH2:26][C:25]2[C:20](=[C:21]([CH2:49][CH2:50][CH3:51])[C:22]([O:28][CH2:29][CH2:30][CH2:31][O:32][C:33]3[C:38]([CH2:39][CH3:40])=[CH:37][C:36]([C:41]4[CH:46]=[CH:45][C:44]([F:47])=[CH:43][CH:42]=4)=[C:35]([OH:48])[CH:34]=3)=[CH:23][CH:24]=2)[O:19]1)=[O:17]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 23501851HCID 23501851, compound

Product 1

HCID 23501852HCID 23501852, compoundYield 110.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-((tert-butoxy)carbonylamino)ethyl-3-((7-(3-(6-ethyl-4-(4-fluorophenyl)-3-hydroxyphenoxy)propoxy)-8-propylchroman-2-yl)carbonylamino)propanoate (55.4 mg, 0.07 mmol) was added to dichloromethane (4 mL), followed by anisole (30 mg, 0.28 mmol) and trifluoroacetic acid (4 mL). The solution was stirred for 2 hours, concentrated under reduced pressure, and purified on a short silica column (chloroform/methanol) to afford 48 mg of product. NMR (CDCl3): 0.90, t (3H); 1.14, t (3H), 1.50, m (2H); 1.62, m (2H); 1.87, m (2H); 2.27, m(3H); 2.54, q (2H); 2.58, m (4H); 3.42, b (2H); 4.14, m (6H); 4.44, b (1H); 6.47, d (1H); 6.57, s (1H); 6.80, m (2H); 6.95, s (1H); 7.10, dd (2H); 7.40, dd (2H); 8.81, b (3H). Mass Spec (EI): m/z=623.4 (M+H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. custompurified on a short silica column (chloroform/methanol)

Sources & evidence

ORD record
ord-b288b16c37714c06af7262fab7188e28
Source dataset
uspto-grants-2002_07
Patent number
US06416733B1

Reaction notes

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