Pyruvic Acid → Mitoglitazone

HRID 341133Notes

Reaction equation

HRID 341133 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6](/[C:9](=N/OC)/[CH2:10][O:11][C:12]2[CH:25]=[CH:24][C:15]([CH2:16][CH:17]3[S:21][C:20](=[O:22])[NH:19][C:18]3=[O:23])=[CH:14][CH:13]=2)=[N:7][CH:8]=1)[CH3:2].C(O)(=O)C(C)=[O:31]>Cl>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9](=[O:31])[CH2:10][O:11][C:12]2[CH:25]=[CH:24][C:15]([CH2:16][CH:17]3[S:21][C:20](=[O:22])[NH:19][C:18]3=[O:23])=[CH:14][CH:13]=2)=[N:7][CH:8]=1)[CH3:2]

Participants

4

Reactant 2

HCID 1060Pyruvic AcidHCID 56835831HCID 56835831, compound

Product 1

HCID 10429242Mitoglitazone

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A stirring solution of 5-(4-{[(2Z)-2-(5-ethylpyridin-2-yl)-2-(methoxyimino)ethyl]oxy}benzyl)-1,3-thiazolidine-2,4-dione (81 mg, 0.20 mmol; Supplier=Kalexsyn; Lot=1003-TTP-194) in 6M HCl (2 ml) and pyruvic acid (0.5 ml) was heated at 75° C. After 2 h at 75° C. HPLC showed reaction was complete. Neutralized with sat'd NaHCO3 and extracted with EtOAc. Extract dried (Na2SO4), filtered and evaporated in vacuo to give 45 mg (60%) pale yellow oil. 1H-NMR (DMSO-d6): δ12.02 (brs, 1H), 8.64 (s, 1H), 7.91 (m, 1H), 7.14 (d, J=8.5 Hz, 2H), 6.88 (d, J=8.5 Hz, 2H), 5.66 (s, 2H), 4.87 (dd, J=9.2, 4.3 Hz, 1H), 3.31 (m, 1H), 3.05 (dd, J=14.1, 9.1 Hz, 1H), 2.74 (q, J=7.7 Hz, 2H), 1.23 (t, J=7.7 Hz, 3H). HPLC (3.860 min., 100 area % @ 210 and 254 nm. MS (ESI—) for C19H18N2O4S m/z 371.3 (M+H)+: m/z 369.4 (M−H)−

Workup

  1. customreaction
  2. extractionNeutralized with sat'd NaHCO3 and extracted with EtOAc
  3. extractionExtract
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto give 45 mg (60%)
  8. custom3.860 min., 100 area

Sources & evidence

ORD record
ord-fbc4406805674168bcdb25648b1b0cd8
Source dataset
uspto-grants-2014_11
Patent number
US08895748B2

Reaction notes

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