Water → HCID 20725640, compound

HRID 1582331Notes

Reaction equation

HRID 1582331 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([N:6]([CH2:15][C@@H:16]2[O:20][C:19](=[O:21])[N:18]([C:22]3[CH:27]=[CH:26][C:25]([C:28]4[CH2:33][CH2:32][N:31]([C:34]([C@@H:36]5[CH2:40][O:39]C(C)(C)[O:37]5)=[O:35])[CH2:30][CH:29]=4)=[C:24]([F:43])[CH:23]=3)[CH2:17]2)C(OCC(Cl)(Cl)Cl)=O)=[N:2]1.O>C(O)(=O)C.[Zn]>[O:1]1[CH:5]=[CH:4][C:3]([NH:6][CH2:15][C@@H:16]2[O:20][C:19](=[O:21])[N:18]([C:22]3[CH:27]=[CH:26][C:25]([C:28]4[CH2:33][CH2:32][N:31]([C:34](=[O:35])[C@@H:36]([OH:37])[CH2:40][OH:39])[CH2:30][CH:29]=4)=[C:24]([F:43])[CH:23]=3)[CH2:17]2)=[N:2]1

Participants

5

Reactant 2

HCID 962WaterHCID 20725699HCID 20725699, compound

Product 1

HCID 20725640HCID 20725640, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a stirred solution of 5(R)-[-N-isoxazol-3-yl-N-(2,2,2-trichloroethyloxycarbonyl)aminomethyl]-3-{3-fluoro-4-[N-(2,2-dimethyl-1,3-dioxolan-4(S)-ylcarbonyl)-1,2,5,6-tetrahydropyrid-4-yl]phenyl}oxazolidin-2-one (200 mg, 0.3 mM) in acetic acid (3 ml) was added zinc dust (195 mg, 3.0 mM). The mixture was stood in an ultrasonic bath for 10 min. then stirred vigorously for 24 hours under a nitrogen atmosphere at ambient temperature. Water (0.5 ml) was added and stirring was continued for a further 24 hours. The reaction mixture was filtered through celite and evaporated. The residue was dissolved in tetrahydrofuran (15 ml)/1.0 M aq. HCl (10 ml) and was stirred at ambient temperature for 3 days. It was evaporated to dryness and the residue was chromatographed by MPLC (8% MeOH/CH2Cl2, gradient to 25%). The title compound was obtained as a white powder on trituration with ether/ethanol (68 mg, 50%). NMR: δ2.42(s, 2H,partially obscured), 3.43(m, 2H), 3.57(m, 1H), 3.79(m, 3H), 4.16(m, 2H), 4.27(m, 1H), 4.38(m, 1H), 4.72(m, 1H), 4.91(m, 1H), 5.00(m, 1H), 6.00(m, 2H), 6.57(t, 1H), 7.30(d of d, 1H), 7.39(t, 1H), 7.50(d of d, 1H), 8.40(s, 1H); m/z ES+(M+H)=447.

Workup

  1. stirringstirring
  2. waitwas continued for a further 24 hours
  3. filtrationThe reaction mixture was filtered through celite
  4. customevaporated
  5. dissolutionThe residue was dissolved in tetrahydrofuran (15 ml)/1.0 M aq. HCl (10 ml)
  6. stirringwas stirred at ambient temperature for 3 days
  7. customIt was evaporated to dryness
  8. customthe residue was chromatographed by MPLC (8% MeOH/CH2Cl2, gradient to 25%)

Sources & evidence

ORD record
ord-f83cd2b1dd9b4b2da9f62b204cc3b88d
Source dataset
uspto-grants-2004_05
Patent number
US06734200B1

Reaction notes

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