Hydrochloric Acid → HCID 131726278, compound

HRID 351385Notes

Reaction equation

HRID 351385 reaction equation
O=[C:2]([C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:40])([F:39])[F:38])[CH:32]=1)[CH2:3][C@@H:4]1[CH2:8][CH2:7][N:6]([C@H:9]2[CH2:14][CH2:13][C@@H:12]([N:15]([CH:17]([CH3:19])[CH3:18])[CH3:16])[CH2:11][C@H:10]2[CH2:20][S:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)(=[O:23])=[O:22])[C:5]1=[O:30].[O:41]([NH2:43])[CH3:42].Cl.CC([O-])=[O:47].[Na+]>CO>[F:38][C:37]([F:40])([F:39])[C:42]([OH:41])=[O:47].[CH:17]([N:15]([CH3:16])[C@@H:12]1[CH2:13][CH2:14][C@H:9]([N:6]2[CH2:7][CH2:8][C@@H:4]([CH2:3][C:2](=[N:43][O:41][CH3:42])[C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:38])([F:40])[F:39])[CH:32]=3)[C:5]2=[O:30])[C@H:10]([CH2:20][S:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)(=[O:23])=[O:22])[CH2:11]1)([CH3:18])[CH3:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 4113O-MethylhydroxylamineHCID 517045Sodium AcetateHCID 69034567HCID 69034567, compound

Product 1

HCID 131726278HCID 131726278, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred mixture of Example 41 (19.7 mg, 34 μmol), methoxylamine.HCl (17 mg, 204 μmol), NaOAc (17 mg, 204 μmol), and MeOH (2 mL) was heated at 50° C. for 24 h. The solvent was removed under vacuum and the residue was dissolved in EtOAc (500 mL). The organic mixture was washed with satd NaHCO3 (3×100 mL), water (200 mL), and brine (200 mL), dried over Na2SO4, filtered, and evaporated. The residue was lyophilized from CH3CN/H2O/TFA give the title compound as a mixture of (E) and (Z) isomers (26.9 mg, 95%): 1H NMR (500 MHz, CDCl3) δ 11.03 (s, 1H), 7.97–7.86 (m, 3H), 7.83–7.76 (m, 1H), 7.70–7.63 (m, 1H), 7.62–7.53 (m, 3H), 7.50–7.41 (m, 1H), 4.32–4.20 (m, 1H), 3.99 (s, 3H), 3.95–3.85 (m, 1H), 3.60–3.43 (m, 2H), 3.32–3.20 (m, 1H), 3.15–2.94 (m, 2H), 2.91–2.77 (m, 2H), 2.75–2.65 (m, 3H), 2.63–2.50 (m, 2H), 2.20–1.68 (m, 7H), 1.50–1.40 (m, 3H), 1.35–1.24 (m, 5H); 19F NMR (282 MHz, CDCl3) δ −63.1, −76.3; ESI MS m/z 608 [C31H40F3N3O4S+H]+.1.

Workup

  1. customThe solvent was removed under vacuum
  2. dissolutionthe residue was dissolved in EtOAc (500 mL)
  3. washThe organic mixture was washed with satd NaHCO3 (3×100 mL), water (200 mL), and brine (200 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-fa7e5c410a844c8b8773b5b785f079e7
Source dataset
uspto-grants-2007_02
Patent number
US07183270B2

Reaction notes

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