Trifluoroacetic acid → HCID 11194903, compound

HRID 481790Notes

Reaction equation

HRID 481790 reaction equation
C1(C)C=CC(S([N:9]2[C@@H:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C@H:10]2[C:18]([O:20][CH3:21])=[O:19])=O)=CC=1.FC(F)(F)C(O)=[O:26]>C(#N)C>[NH2:9][C@@H:10]([C@@H:11]([OH:26])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:18]([O:20][CH3:21])=[O:19]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 10245181HCID 10245181, compound

Product 1

HCID 11194903HCID 11194903, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
45 °C

Procedure

Into a 50-mL round-bottomed flask equipped with a magnetic stir bar were placed 0.315 g (1.0 mmol) (2S,3S)-(+)-N-(p-toluenesulfinyl)-2-carbomethoxy-3-phenylaziridine (prepared according to Example 1), 10 mL acetonitrile and 2 mL 50% aqueous trifluoroacetic acid. The reaction mixture was stirred for 6 h at 45° C., the solvent was removed and the residue treated with H2O (5 mL). After washing the aqueous solution with ether (2×10 mL), the aqueous phase was brought to pH 10 with concentrated NH4OH and extracted with CHCl3 (2×10 mL). After drying (MgSO4), the organic phase was filtered and concentrated to give the titled compound in impure form, which was purified by flash chromatography (ether:CH3CN:NH4OH; 10:1:0.2) to afford the titled compound (0.138 g, 71%) as a viscous oil: [α]D20 +11.0° (c 1.8, MeOH) ([α]D20 -10.97° (c 1.4, MeOH) according to Beulshausen, T. et al. Liebigs Ann. Chem. 1991, 1207 for the (2R,3S)-isomer); 1H NMR (CDCl3) δ2.10 (bs, 3H, NH2, OH) 3.65 (d, J=4.5 Hz, 1H, CH), 3.69 (s, 3H, CH3), 4.91 (d, J=4.5 Hz, 1H, CH) 7.36-7.26 (m, 5H, aromatic); 13C NMR (CDCl3) δ52.2, 60.6, 74.1, 126.0, 127.8, 128.4, 140.9, 173.7.

Workup

  1. customInto a 50-mL round-bottomed flask equipped with a magnetic stir bar
  2. customthe solvent was removed
  3. additionthe residue treated with H2O (5 mL)
  4. washAfter washing the aqueous solution with ether (2×10 mL)
  5. extractionextracted with CHCl3 (2×10 mL)
  6. dry with materialAfter drying (MgSO4)
  7. filtrationthe organic phase was filtered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-6b667a1fb89b47d8956386eca7a5198a
Source dataset
uspto-grants-1998_08
Patent number
US05789599

Reaction notes

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