Trifluoroacetic acid → Trifluoroacetic acid

HRID 2213369Notes

Reaction equation

HRID 2213369 reaction equation
[C:1]([OH:7])([C:3]([F:6])([F:5])[F:4])=[O:2].C(OC(=O)[NH:14][CH2:15][CH:16]1[O:20][C:19](=[O:21])[N:18]([C:22]2[CH:27]=[CH:26][C:25]([N:28]3[CH:33]=[CH:32][C:31](=[O:34])[CH2:30][CH2:29]3)=[CH:24][CH:23]=2)[CH2:17]1)(C)(C)C>ClCCCl>[C:1]([OH:7])([C:3]([F:6])([F:5])[F:4])=[O:2].[NH2:14][CH2:15][CH:16]1[O:20][C:19](=[O:21])[N:18]([C:22]2[CH:27]=[CH:26][C:25]([N:28]3[CH:33]=[CH:32][C:31](=[O:34])[CH2:30][CH2:29]3)=[C:24]([F:4])[CH:23]=2)[CH2:17]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21051178HCID 21051178, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 21957319HCID 21957319, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

TFA (1 mL) is added to a solution of {3-[4-(4-oxo-3,4-dihydro-2H-pyridin-1-yl)-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-carbamic acid tert-butyl ester (200 mg, 0.52 mmol) in DCE (4 mL). This solution is stirred for 1.5 h, and the mixture is concentrated under vacuum to afford TFA salt of 1-[4-(5-Aminomethyl-2-oxo-oxazolidin-3-yl)-2-fluoro-phenyl]-2,3-dihydro-1H-pyridin-4-one. TEA (105 mg, 1.04 mmol) is added to a solution of the above salt in MeOH (4.0 mL) followed by difluorothioacetic acid-O-(3,3-diphenyl-propyl)ester (84 mg, 0.25 mmol). The mixture is stirred for 4 h at 50° C., and the solvent is removed under vacuum. The crude product is purified by silica gel column chromatography (eluent: 1.5% MeOH in EtOAc). MS (m/z): 382 [M+1]+. 1H NMR (300 MHz, DMSO-d6) δ7.93 (d, J=7.7 Hz, 1H), 7.73 (d, J=9.3 Hz, 2H), 7.49 (d, J=9.3 Hz, 2H), 6.69 (t, J=55.2 Hz, 1H), 5.21–5.17 (m, 2H), 4.38 (t, J=9.1 Hz, 1H), 4.18–4.12 (m, 4H), 4.05 (dd, J=6.3 and 9.1 Hz, 1H), 3.48 (d, J=7.1 Hz, 2H).

Workup

  1. concentrationthe mixture is concentrated under vacuum

Sources & evidence

ORD record
ord-e9af32e6a6e8494ba6ef1353b29d9f39
Source dataset
uspto-grants-2006_09
Patent number
US07105547B2

Reaction notes

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