HCID 66716745, compound → HCID 11562778, compound

HRID 1028618Notes

Reaction equation

HRID 1028618 reaction equation
[O:1]1CCCO[CH:2]1[C:7]1[CH:8]=[C:9]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][C:21]=3[C:30]3[CH:35]=[C:34]([CH:36]([CH3:38])[CH3:37])[C:33]([F:39])=[CH:32][C:31]=3[O:40][CH3:41])[C@H:14]2[CH3:42])[CH:10]=[CH:11][CH:12]=1>C1COCC1.Cl.CCOC(C)=O>[F:39][C:33]1[C:34]([CH:36]([CH3:38])[CH3:37])=[CH:35][C:30]([C:21]2[CH:22]=[CH:23][C:24]([C:26]([F:29])([F:27])[F:28])=[CH:25][C:20]=2[CH2:19][N:15]2[C@@H:14]([CH3:42])[C@@H:13]([C:9]3[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=3)[CH:2]=[O:1])[O:17][C:16]2=[O:18])=[C:31]([O:40][CH3:41])[CH:32]=1

Participants

5

Reactant 1

HCID 66716745HCID 66716745, compound

Product 1

HCID 11562778HCID 11562778, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The solution of (4S,5R)-5-[3-(1,3-dioxan-2-yl)phenyl]-3-{[4′-fluoro-5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}-4-methyl-1,3-oxazolidin-2-one (EXAMPLE 210) (380 mg, 0.647 mmol) in THF and 1N HCl (3:1) (4 mL) was stirred at room temperature for 2 h. The reaction mixture was diluted with EtOAc and washed with NaHCO3 and brine. The organic layer was dried and concentrated in vacuo. The crude material was purified by flash chromatography (Si) to provide 3-((4S,5R)-3-{[4′-fluoro-5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}-4-methyl-2-oxo-1,3-oxazolidin-5-yl)benzaldehyde. LCMS calc.=530.19; found=530.4 (M+1)+. 1H NMR (500 MHz, CDCl3, 1:1 mixture of atropisomers) δ 10.03 (s, 1 H); 7.88 (s, 0.5 H); 7.87 (s, 0.5 H); 7.77-7.52 (m, 5 H); 7.37 (d, J=3.5 Hz, 0.5 H); 7.36 (d, J=3.4 Hz, 0.5 H); 7.02 (d, J=8.4 Hz, 0.5 H); 6.99 (d, J=8.4 Hz, 0.5 H); 6.71 (d, J=3.5 Hz, 0.5 H); 6.69 (d, J=3.4 Hz, 0.5 H); 4.17 (d, J=15.8 Hz, 0.5 H); 6.98 (d, J=15.8 Hz, 0.5 H); 3.78 (s, 3 H); 3.85-3.71 (m, 1 H); 3.26-3.19 (m, 1 H); 1.30-1.26 (m, 4.5 H); 1.19 (d, J=6.9 Hz, 1.5 H); 0.53 (d, J=6.6 Hz, 1.5 H); 0.40 (d, J=6.6 Hz, 1.5 H).

Workup

  1. washwashed with NaHCO3 and brine
  2. customThe organic layer was dried
  3. concentrationconcentrated in vacuo
  4. customThe crude material was purified by flash chromatography (Si)

Sources & evidence

ORD record
ord-d87e8c3e270c4ed698661accbba9bd49
Source dataset
uspto-grants-2014_05
Patent number
US08735435B2

Reaction notes

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