HCID 20725697, compound → HCID 20725707, compound

HRID 1582328Notes

Reaction equation

HRID 1582328 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]([CH:34]=[O:35])[CH2:30][CH:29]=4)=[C:24]([F:36])[CH:23]=3)[CH2:17]2)C(OCC(Cl)(Cl)Cl)=O)=[N:2]1>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]([CH:34]=[O:35])[CH2:30][CH:29]=4)=[C:24]([F:36])[CH:23]=3)[CH2:17]2)=[N:2]1

Participants

4

Reactant 1

HCID 20725697HCID 20725697, compound

Product 1

HCID 20725707HCID 20725707, 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-(1-formyl-1,2,5,6-tetrahydropyrid-4-yl)phenyl]oxazolidin-2-one (110 mg, 0.2 mM) in acetic acid (3 ml) was added zinc dust (130 mg, 2.0 mM). The mixture was held in an ultrasonic bath for 10 min. and then stirred vigorously for 48 hours under a nitrogen atmosphere at ambient temperature. The mixture was filtered through celite and the filtrate was evaporated. The residue was taken into 5% MeOH/CH2Cl2 (5 ml) with filtration of inorganic material and the title compound was isolated by MPLC (4% MeOH/CH2Cl2). It was obtained as a brittle glass on evaporation under high vacuum (22 mg, 28%). NMR: 2.41(s, 2H), 3.45(m, 2H), 3.60(m, 2H), 3.84(t, 1H), 4.08(m, 2H), 4.19(t,1H), 4.91 (m, 1H), 6.00(m, 2H), 6.53(m, 1H), 7.36(m, 2H), 7.54(d, 2H), 8.11 & 8.19(2s, 1H), 8.37(s, 1H); m/z ES+(M+H)=387.

Workup

  1. filtrationThe mixture was filtered through celite
  2. customthe filtrate was evaporated
  3. filtrationThe residue was taken into 5% MeOH/CH2Cl2 (5 ml) with filtration of inorganic material

Sources & evidence

ORD record
ord-19e8420b396343f4bace07fac898e61d
Source dataset
uspto-grants-2004_05
Patent number
US06734200B1

Reaction notes

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