Potassium Carbonate → HCID 131729985, compound

HRID 2062133Notes

Reaction equation

HRID 2062133 reaction equation
C(=O)([O-])[O-].[K+].[K+].C([O:10][C@@H:11]1[C@@H:20]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C@@H:19]([N:29]=[N+:30]=[N-:31])[C@@H:18]([CH2:32][O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[O:17][C@H:12]1[O:13]C(=O)C)(=O)C>CO.O>[N:29]([C@H:19]1[C@@H:18]([CH2:32][O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[O:17][CH:12]([OH:13])[C@H:11]([OH:10])[C@H:20]1[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[N+:30]=[N-:31]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 86659939HCID 86659939, compound

Product 1

HCID 131729985HCID 131729985, compoundYield 84.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Potassium carbonate (0.600 g, 4.34 mmol, 3.99 equiv) was added to a solution of diacetate 222 (0.511 g, 1.09 mmol, 1.00 equiv) in methanol (50 mL) and water (5 mL). After 1.5 h, the yellow solution was decanted from the undissolved potassium carbonate and concentrated to about 4 mL and then diluted with dichloromethane (50 mL) and washed with saturated aqueous sodium bicarbonate solution (10 mL). The aqueous layer was extracted with dichloromethane (2×10 mL) and the combined organic layers were dried with magnesium sulfate and purified by silica gel chromatography (ethyl acetate) to afford 223 (0.353 g, 0.917 mmol, 84% yield) as a yellow oil (1:1 α:β). Rf=0.17, 014 (hexane/ethyl acetate 1:1); 1H NMR (400 MHz, CDCl3) δ 7.43-7.27 (m, 20H), 5.28 (d, J=3.8, 1H), 4.78 (d, J=11.5, 1H), 4.78 (d, J=11.5, 1H), 4.67 (d, J=11.5, 1H), 4.68 (d, J=11.5, 1H), 4.58 (d, J=11.9, 1H), 4.56 (d, J=11.9, 1H), 4.52 (d, J=11.9, 1H), 4.51 (d, J=11.9, 1H), 4.51 (d, J=7.7, 1H), 4.21 (td, J=6.5, 1.1, 1H), 4.02 (dd, J=3.4, 1.3, 1H), 3.99 (dd, J=9.9, 3.8, 2H), 3.85 (dd, J=9.7, 3.5, 1H), 3.73 (dd, J=9.5, 7.7, 1H), 3.69-3.51 (m, 6H); 13C NMR (126 MHz, CDCl3) δ 137.62, 137.50, 137.48, 128.67, 128.59, 128.16, 128.13, 128.10, 128.09, 128.07, 128.02, 128.00, 97.08, 92.50, 80.85, 78.06, 73.64, 73.61, 72.63, 72.51, 72.14, 71.82, 69.25, 68.76, 68.68, 67.38, 60.27, 59.49; FTIR (neat film) 3401.3, 3032.4, 2921.6, 2105.6, 1454.4, 1367.2, 1279.3, 1095.8, 1028.3, 738.1, 698.0 cm−1; HRMS (ESI) m/z: Calcd for C20H23N3O5Na (M+Na+) 408.1535, found 408.1535.

Workup

  1. customthe yellow solution was decanted from the undissolved potassium carbonate
  2. concentrationconcentrated to about 4 mL
  3. additiondiluted with dichloromethane (50 mL)
  4. washwashed with saturated aqueous sodium bicarbonate solution (10 mL)
  5. extractionThe aqueous layer was extracted with dichloromethane (2×10 mL)
  6. dry with materialthe combined organic layers were dried with magnesium sulfate
  7. custompurified by silica gel chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-295887bb3ae14e5891a7d9e20ca1a2e8
Source dataset
uspto-grants-2012_10
Patent number
US08283456B2

Reaction notes

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