Trifluoroacetic acid → HCID 59275651, compound

HRID 555037Notes

Reaction equation

HRID 555037 reaction equation
C(O)(C(F)(F)F)=O.C([O:12][C:13]([C:15]1[CH:16]=[C:17]([C:21]2[C:22]([N:42]([CH3:47])[S:43]([CH3:46])(=[O:45])=[O:44])=[CH:23][C:24]3[O:28][C:27]([C:29]4[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=4)=[C:26]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[C:25]=3[CH:41]=2)[CH:18]=[CH:19][CH:20]=1)=[O:14])(C)(C)C>ClCCCl>[CH2:39]([O:38][C:36]([C:26]1[C:25]2[CH:41]=[C:21]([C:17]3[CH:16]=[C:15]([CH:20]=[CH:19][CH:18]=3)[C:13]([OH:14])=[O:12])[C:22]([N:42]([CH3:47])[S:43]([CH3:46])(=[O:45])=[O:44])=[CH:23][C:24]=2[O:28][C:27]=1[C:29]1[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=1)=[O:37])[CH3:40]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59275410HCID 59275410, compound

Product 1

HCID 59275651HCID 59275651, compoundYield 102.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

TFA (2 mL, 26.0 mmol) was added to a stirring solution of ethyl 5-(3-(tert-butoxycarbonyl)phenyl)-2-(4-fluorophenyl)-6-(N-methylmethylsulfonamido)benzofuran-3-carboxylate (100 mg, 0.176 mmol) in DCE (9 mL) at 25° C. It was allowed to stir for several hours then concentrated to give the titled compound (92 mg, quant). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.05-8.12 (3H, m), 7.92-8.03 (3H, m), 7.65-7.75 (1H, m), 7.53-7.64 (1H, m), 7.44 (2H, t, J=8.91 Hz), 4.33 (2H, q, J=7.03 Hz), 3.12 (3H, s), 2.93 (3H, s), 1.26 (3H, t, J=7.15 Hz). LC-MS retention time: 1.17 min; m/z (MH−): 510. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Waters XBridge 5u C18 4.6×50 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 5 ml/min, a gradient of 100% solvent A/0% solvent B to 0% solvent A/100% solvent B, a gradient time of 2 min, a hold time of 1 min, and an analysis time of 3 min where solvent A was 5% acetonitrile/95% H2O/10 mM ammonium acetate and solvent B was 5% H2O/95% acetonitrile/10 mM ammonium acetate. MS data was determined using a MICROMASS® Platform for LC in electrospray mode.

Workup

  1. concentrationthen concentrated

Sources & evidence

ORD record
ord-7e9504e765b047efb4ce67bb6fad6d87
Source dataset
uspto-grants-2011_11
Patent number
US08048887B2

Reaction notes

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