Trifluoroacetic acid → HCID 21957321, compound

HRID 2213355Notes

Reaction equation

HRID 2213355 reaction equation
C(O)(C(F)(F)F)=O.C([O:12][C:13](=[O:33])[C:14]1[C:19]([F:20])=[CH:18][C:17]([N:21]2[CH2:25][CH:24]([CH2:26][NH:27][C:28](=[O:30])[CH3:29])[O:23][C:22]2=[O:31])=[CH:16][C:15]=1[F:32])(C)(C)C>C(Cl)Cl>[C:28]([NH:27][CH2:26][CH:24]1[O:23][C:22](=[O:31])[N:21]([C:17]2[CH:16]=[C:15]([F:32])[C:14]([C:13]([OH:33])=[O:12])=[C:19]([F:20])[CH:18]=2)[CH2:25]1)(=[O:30])[CH3:29]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69586011HCID 69586011, compound

Product 1

HCID 21957321HCID 21957321, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (10 mL) is added with stirring to a solution of 4-[5-(acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2,6-difluoro-benzoic acid tert-butyl ester (1.44 g, 3.88 mmol) in DCM (20 mL). The resulting solution is stirred for 1 h, and the volatiles removed under vacuum to afford 4-[5-(acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2,6-difluoro-benzoic acid as a white solid (1.20 g). The acid intermediate is dissolved in dry t-BuOH (15 mL). Diphenylphosphoryl azide (1 mL, 4.65 mmol) and TEA (1.62 mL, 11.64 mmol) are added. The mixture is heated at reflux for 3 h and allowed to cool down to r.t. Solvent is removed under vacuum. The compund, N-[3-(4-tert-butoxycarbonylamino-3,5-difluoro-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide, is purified by silica gel column chromatography (eluent—EtOAc). The compound is dissolved in DCM (20 mL); and TFA (10 mL) is added. The reaction is stirred at r.t. for 1 h, and the volatiles are removed under vacuum. The crude aniline is purified by silica gel column chromatography (EtOAc) to afford the pure title compound. MS (m/z): 286 [M+H]+. 1H NMR (300 MHz, CDCl3) δ 2.16 (s, 3H), 3.73–3.74 (m, 2H), 3.90–3.96 (m, 1H), 4.26 (t, J=9.0 Hz, 1H), 4.93–5.01 (m, 1H), 7.32 (d, 8.7 Hz, 2H).

Workup

  1. customthe volatiles removed under vacuum

Sources & evidence

ORD record
ord-0d28231d0a31434c82f7be6a4142dddb
Source dataset
uspto-grants-2006_09
Patent number
US07105547B2

Reaction notes

Loading…