Potassium Carbonate → HCID 389495, compound

HRID 2051035Notes

Reaction equation

HRID 2051035 reaction equation
[C:1]([NH:4][C:5]1[C:20]([CH3:21])=[CH:19][C:8]2[N:9]3[CH2:14][CH2:13][CH:12](CC([O-])=O)[C:10]3=[N:11][C:7]=2[C:6]=1[N+:22]([O-:24])=[O:23])(=[O:3])[CH3:2].C([O-])([O-])=[O:26].[K+].[K+]>CO>[C:1]([NH:4][C:5]1[C:20]([CH3:21])=[CH:19][C:8]2[N:9]3[CH2:14][CH2:13][CH:12]([OH:26])[C:10]3=[N:11][C:7]=2[C:6]=1[N+:22]([O-:24])=[O:23])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 19834489HCID 19834489, compound

Product 1

HCID 389495HCID 389495, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 205 mg (0.61 mmol) of 15b in 10 mL of dry methanol was added 88 mg of K2CO3. The reaction was stirred at room temperature for 20 min and then concentrated in vacuo. The black residue was flash chromatographed on silica gel using a chloroform/methanol (98:2) mixture as the eluant. The yellow-colored product was recrystallized by dissolving it in a minimum amount of (4:1) chloroform/methanol, adding hexane, and then chilling: 141 mg (78%) yield: dec pt 259° C.; TLC (chloroform:methanol[20:80]) Rf =0.35, IR(KBr pellet) 3237, 3181, 3065, 1741, 1700, 1667, 1632, 1574, 1532, 1404 cm-1 ; 1H NMR (dimethyl sulfoxide-d6) δ9.67 (1 H, s, amide proton), 7.66 (1 H, s, C(8) proton), 5.97 (1 H, d, J= 5.3 Hz, hydroxyl proton), 5.09 (1 H, m, C(3) proton), 4.22 and 4.05 (2 H, 2×m, C(1) diastereomeric methylene), 2.90 and 2.37 (2 H, 2×m, C(2) diastereomeric methylene), 2.27 (3 H, s, 7-methyl proton), 1.97 (3 H, s, acetamido methyl); mass spectrum (EI mode) m/z, 290(P+), 272(P+ -H2O), 248 (P+ -ketene) 244 (P+ -NO2) Anal. Calcd for C13H14N4O4.0.75H2O: C, 51.39; H, 5.13; N, 18.44. Found: C, 51.75; H, 4.77; N, 18.45.

Workup

  1. concentrationconcentrated in vacuo
  2. customchromatographed on silica gel using a chloroform/methanol (98:2) mixture as the eluant
  3. customThe yellow-colored product was recrystallized
  4. dissolutionby dissolving it in a minimum amount of (4:1) chloroform/methanol
  5. additionadding hexane
  6. temperaturechilling

Sources & evidence

ORD record
ord-31d6400a7169406bb1f4486e6b2320bf
Source dataset
uspto-grants-1991_05
Patent number
US05015742

Reaction notes

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