Ethyl formate → HCID 20725697, compound

HRID 1582330Notes

Reaction equation

HRID 1582330 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][NH:31][CH2:30][CH:29]=4)=[C:24]([F:34])[CH:23]=3)[CH2:17]2)[C:7]([O:9][CH2:10][C:11]([Cl:14])([Cl:13])[Cl:12])=[O:8])=[N:2]1.C(N(CC)CC)C.[CH:42](OCC)=[O:43]>>[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:42]=[O:43])[CH2:30][CH:29]=4)=[C:24]([F:34])[CH:23]=3)[CH2:17]2)[C:7]([O:9][CH2:10][C:11]([Cl:14])([Cl:12])[Cl:13])=[O:8])=[N:2]1

Participants

4

Reactant 3

HCID 8025Ethyl formate2×HCID 8471TriethylamineHCID 20725694HCID 20725694, compound

Product 1

HCID 20725697HCID 20725697, compoundYield 117%

Procedure

To a suspension of 5(R)-[N-isoxazol-3-yl-N-(2,2,2-trichloroethyloxycarbonyl)aminomethyl]-3-[3-fluoro-4-(1,2,5,6-tetrahydropyrid-4-yl)phenyl]oxazolidin-2-one (100 mg, 0.175 mmol) in ethyl formate (5 ml), with stirring was added, triethylamine (20 mg, 27 μl, 0.2 mmol), and the mixture was heated to reflux overnight. Ethyl formate was added and the mixture washed with 2M hydrochloric acid and saturated brine, dried over sodium sulfate and concentrated by rotary evaporation to give the crude title compound as a yellow gum (115 mg, 117%). M/z ES+(M+H)=561.

Workup

  1. additionwas added
  2. temperatureto reflux overnight
  3. washthe mixture washed with 2M hydrochloric acid and saturated brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-075c4886609e4a1c985d8f56103db85b
Source dataset
uspto-grants-2004_05
Patent number
US06734200B1

Reaction notes

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