Potassium Carbonate → HCID 69081709, compound

HRID 1396263Notes

Reaction equation

HRID 1396263 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:17]([CH2:18][O:19]CC2C=CC=CC=2)[O:16][C@H:15]2[C@H:11]([N:12]=[C:13]([N:27]([CH3:29])[CH3:28])[S:14]2)[C@H:10]1[O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+]>CC(OC(C)=O)=O.CC(O)=O.CO.[Cl-].[Cl-].[Zn+2]>[CH2:1]([O:8][C@@H:9]1[C@@H:17]([CH2:18][OH:19])[O:16][C@H:15]2[C@H:11]([N:12]=[C:13]([N:27]([CH3:29])[CH3:28])[S:14]2)[C@H:10]1[O:30][CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 2

HCID 11430Potassium CarbonateHCID 69084122HCID 69084122, compound

Product 1

HCID 69081709HCID 69081709, compoundYield 84%

Reagents, catalysts & solvents 4

HCID 3007855ZincchlorideCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 7918Acetic AnhydrideSolvent

Procedure

To a solution of 92 (166 g, 0.3 mol) in Ac2O (1 L) and AcOH (100 mL) was added anhydrous ZnCl2 (353 g, 2.6 mol) at 0° C. After kept additional 2 hours at room temperature, the reaction was poured into ice-cold H2O (1.5 kg) slowly and extracted with dichloromethane (3×500 mL). The organic layers combined, washed with brine (3×200 mL) and dried over anhydrous sodium sulfate. After filtration, volatiles were distilled out by high vacuum to give crude 93 (160 g, (ES, m/z) [M+H]+ 471.0) as a brown oil. A solution of the above crude 93 in methanol (1 L) was treated with K2CO3 (18 g, 0.13 mol) at 30° C. for 8 hours, after filtration, the solvent was distilled out under vacuum to give a residue, which was purified by a silica gel column with 20%-30% ethyl acetate in petroleum ether to afford the title compound (94) (108 g, 79% 2 steps) as a yellow syrup; (ES, m/z) [M+H]+ 429.0; 1H NMR (300 MHz, CDCl3) δ 7.26-7.43 (m, 10H), 6.29 (d, J=6.6 Hz, 1H), 4.54-4.81 (m, 4H), 4.41 (d, J=4.8 Hz, 1H), 4.17-4.18 (m, 1H), 3.57-3.79 (m, 4H), 3.02 (s, 6H).

Workup

  1. extractionextracted with dichloromethane (3×500 mL)
  2. washwashed with brine (3×200 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationAfter filtration, volatiles
  5. distillationwere distilled out by high vacuum
  6. customto give crude 93 (160 g, (ES, m/z) [M+H]+ 471.0) as a brown oil
  7. filtrationafter filtration
  8. distillationthe solvent was distilled out under vacuum
  9. customto give a residue, which
  10. customwas purified by a silica gel column with 20%-30% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-8c1e418866a14f3285ccf93e7928256d
Source dataset
uspto-grants-2014_12
Patent number
US08901087B2

Reaction notes

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