Potassium Carbonate → HCID 58316596, compound

HRID 2382629Notes

Reaction equation

HRID 2382629 reaction equation
[C:1]([O:4][CH:5]([C:11]1[CH:16]=[CH:15][C:14]([C@@H:17]2[C@@H:21]([CH2:22]/[CH:23]=[CH:24]\[CH2:25][CH2:26][CH2:27][C:28]([O:30][CH3:31])=[O:29])[CH2:20][CH2:19][C@H:18]2[O:32]C(=O)C2C=CC([N+]([O-])=O)=CC=2)=[CH:13][CH:12]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])(=[O:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[NH4+].[Cl-]>CO>[CH3:31][O:30][C:28](=[O:29])[CH2:27][CH2:26][CH2:25]/[CH:24]=[CH:23]\[CH2:22][C@H:21]1[CH2:20][CH2:19][C@@H:18]([OH:32])[C@@H:17]1[C:14]1[CH:13]=[CH:12][C:11]([CH:5]([O:4][C:1](=[O:3])[CH3:2])[CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 59815107HCID 59815107, compound

Product 1

HCID 58316596HCID 58316596, compoundYield 67.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 27 (53 mg, 0.09 mmol) and K2CO3 (7 mg, 0.05 mmol) in CH3OH (2.6 mL) was stirred for 1 h. Saturated NH4Cl solution (20 mL) was added and the resulting mixture was extracted with ethyl acetate (3×20 mL). The combined ethyl acetate solution was dried (Na2SO4), filtered and evaporated. The residue was purified by flash chromatography on silica gel (40% ethyl acetate/hexanes) to give compound 28 (27 mg, 67%) along with the deacetylated side product (9 mg, 26%).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate (3×20 mL)
  2. dry with materialThe combined ethyl acetate solution was dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by flash chromatography on silica gel (40% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-ef0bcc401519495e9362c467bbfdb8de
Source dataset
uspto-grants-2012_09
Patent number
US08263593B2

Reaction notes

Loading…