Acetic Acid → HCID 86697929, compound

HRID 338114Notes

Reaction equation

HRID 338114 reaction equation
C(O)(=O)C.[C:5]([O:9][C:10]([N:12]1[CH2:19][CH:18]2[C:14]([C:31]3[S:32][CH:33]=[CH:34][CH:35]=3)([N:15]([C:20](=[S:30])[NH:21][C:22](=[O:29])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[O:16][CH2:17]2)[CH2:13]1)=[O:11])([CH3:8])([CH3:7])[CH3:6].C(=O)(O)[O-].[Na+]>[Zn].O>[C:22]([NH:21][C:20]([NH:15][C:14]1([C:31]2[S:32][CH:33]=[CH:34][CH:35]=2)[CH:18]([CH2:17][OH:16])[CH2:19][N:12]([C:10]([O:9][C:5]([CH3:8])([CH3:7])[CH3:6])=[O:11])[CH2:13]1)=[S:30])(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 86697930HCID 86697930, compound

Product 1

HCID 86697929HCID 86697929, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

Acetic acid (104 mL) is added to tert-butyl-1-(benzoylcarbamothioyl)-6a-(2-thienyl)-3,3a,4,6-tetrahydropyrrolo[3,4-c]isoxazole-5-carboxylate followed by powdered zinc (17.1 g, 261 mmol) and the resulting suspension is vigorously stirred at 40° C. for 7 hours followed by an additional hour at 45-50° C. The reaction is concentrated under reduced pressure. To the crude reaction mixture is added diatomaceous earth and water, followed by a saturated solution of sodium bicarbonate. The mixture is filtered and washed with ethyl acetate. The filtrate is extracted with ethyl acetate. The organic layers are combined, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give a residue. The residue is purified by silica gel flash chromatography, eluting with hexane/ethyl acetate (1:0) to hexane/ethyl acetate (0:1) to give the title compound (3.8 g, 32%). ES/MS (m/e): 460 (M−1).

Workup

  1. waitfollowed by an additional hour at 45-50° C
  2. concentrationThe reaction is concentrated under reduced pressure
  3. customTo the crude reaction mixture
  4. filtrationThe mixture is filtered
  5. washwashed with ethyl acetate
  6. extractionThe filtrate is extracted with ethyl acetate
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customto give a residue
  11. customThe residue is purified by silica gel flash chromatography
  12. washeluting with hexane/ethyl acetate (1:0) to hexane/ethyl acetate (0:1)

Sources & evidence

ORD record
ord-52249499696742259ee5dea2fa299d9b
Source dataset
uspto-grants-2014_11
Patent number
US08889856B2

Reaction notes

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