Ethyl Acetate → HCID 10151302, compound

HRID 1268978Notes

Reaction equation

HRID 1268978 reaction equation
[O:1]=[S:2]1(=[O:25])[CH2:7][CH:6]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][N:20]=[N+:21]=[N-:22])[O:16][C:15]3=[O:23])=[CH:10][C:9]=2[F:24])[CH2:4][CH2:3]1.C([O:30][C:31](=[O:34])[C:32]#[CH:33])(C)(C)C.C(OCC)(=O)C>O1CCOCC1>[O:25]=[S:2]1(=[O:1])[CH2:3][CH:4]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][N:20]4[CH:33]=[C:32]([C:31]([OH:34])=[O:30])[N:22]=[N:21]4)[O:16][C:15]3=[O:23])=[CH:10][C:9]=2[F:24])[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 543038tert-Butyl propiolateHCID 11222326HCID 11222326, compound

Product 1

HCID 10151302HCID 10151302, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(5R)-3-[4-(1,1-Dioxo-3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-5-(azidomethyl)oxazolidin-2-one (6.9 g, 18.83 mmol) (Reference Example 2) was dissolved in dry 1,4-dioxane (15 ml), 2-propynoic acid t-butylester (4.75 g, 37.67 mmol) was added and the resulting mixture was refluxed for 12 hours under vigorous stirring. Ethyl acetate (30 ml) was added and the resulting precipitate was filtered, washed with ethyl acetate and dried as a white solid (5 g). This solid was suspended in dichloromethane (16 ml), followed by drop wise addition of trifluoroacetic acid (8 ml) and the resulting mixture was stirred over night. The solvent was removed under vacuum and the residue was purified by precipitation from dichloromethane to give the title product as an off-white solid (3.3 g).

Workup

  1. temperaturethe resulting mixture was refluxed for 12 hours under vigorous stirring
  2. filtrationthe resulting precipitate was filtered
  3. washwashed with ethyl acetate
  4. dry with materialdried as a white solid (5 g)
  5. additionfollowed by drop wise addition of trifluoroacetic acid (8 ml)
  6. customThe solvent was removed under vacuum
  7. customthe residue was purified by precipitation from dichloromethane

Sources & evidence

ORD record
ord-640bc3d2b2ec48d39a51dc3baa91c4bd
Source dataset
uspto-grants-2007_04
Patent number
US07199143B2

Reaction notes

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