Trifluoroacetic acid → HCID 10021589, compound

HRID 2213366Notes

Reaction equation

HRID 2213366 reaction equation
C(O)(C(F)(F)F)=O.[C:8]([O:12][C:13](=[O:36])[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)=[C:24]([F:35])[CH:23]=2)[CH2:17]1)(C)(C)C.ClC(OC)=O>ClC(Cl)C.CC#N>[CH3:8][O:12][C:13](=[O:36])[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:29]=[CH:30][C:31](=[O:34])[CH2:32][CH2:33]3)=[C:24]([F:35])[CH:23]=2)[CH2:17]1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 6586Methyl chloroformateHCID 21051176HCID 21051176, compound

Product 1

HCID 10021589HCID 10021589, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 63651,1-DichloroethaneSolvent

Procedure

TFA (1.5 mL) is added to a solution of {3-[3-fluoro-4-(4-oxo-3,4-dihydro-2H-pyridin-1-yl)-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-carbamic acid tert-butyl ester (300 mg, 0.74 mmol) in dichloroethane (6.0 mL). This solution is stirred for 1.5 h. Removed solvent under vacuum, and the residue is dissolved in MeCN (3.0 mL). TEA (0.41 mL, 3 mmol) is added followed by methyl chloroformate (98 mg, 1 mmol). The mixture is stirred at r.t. for 16 h. Solvent is removed under vacuum, and the residue is purified by silica gel column chromatography (eluent: EtOAc) to afford the product as a yellow solid. Yield 100 mg (37%). MS (m/z): 364 [M+1]+. 1H NMR (300 MHz, DMSO-d6) δ7.62–7.30 (m, 4H), 4.98 (dd, J=7.7 Hz, 3.0 Hz, 1H), 4.80–4.65 (m, 1H), 4.11 (dd, J=6.86 Hz, 2H), 3.79–3.74 (m, 1H), 3.53 (s, 3H), 3.40–3.30 (m, 2H), 2.49–2.44 (m, 2H).

Workup

  1. stirringThe mixture is stirred at r.t. for 16 h
  2. customSolvent is removed under vacuum
  3. customthe residue is purified by silica gel column chromatography (eluent: EtOAc)

Sources & evidence

ORD record
ord-e21ce2c5acbb4cf9b69b300d56e1aa8c
Source dataset
uspto-grants-2006_09
Patent number
US07105547B2

Reaction notes

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