Potassium Carbonate → HCID 10648237, compound

HRID 842260Notes

Reaction equation

HRID 842260 reaction equation
[C:1]([O:4][CH2:5][CH2:6][C:7]([NH:32][C:33](=[O:35])[CH3:34])([CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23](=O)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:19][CH:18]=1)[CH2:8][CH2:9][CH2:10][O:11][C:12](=[O:14])[CH3:13])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>FC(F)(F)C(O)=O.C([SiH](CC)CC)C>[C:1]([O:4][CH2:5][CH2:6][C:7]([NH:32][C:33](=[O:35])[CH3:34])([CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:19][CH:18]=1)[CH2:8][CH2:9][CH2:10][O:11][C:12](=[O:14])[CH3:13])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 226186813-Acetamido-6-acetoxy-3-[2-(4-octanoylphenyl)ethyl]hexyl acetate

Product 1

HCID 10648237HCID 10648237, compoundYield 64.3%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 12052TriethylsilaneSolvent

Procedure

To a solution of 3-acetamido-6-acetoxy-3-[2-(4-octanoylphenyl)ethyl]hexyl acetate (720 mg) in trifluoroacetic acid (15 ml), triethylsilane (0.53 ml) was added at room temperature. After stirring for an hour, the reaction solution was poured into ice-water and potassium carbonate was carefully added to the mixture to neutralize. The mixture was extracted with ethyl acetate and the extract was washed with water and a saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled away and the residue obtained was purified by silica gel chromatography (eluent; hexane-ethyl acetate=1:1) to give the subject compound (450 mg) as a colorless oily substance.

Workup

  1. additionwas carefully added to the mixture
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe extract was washed with water
  4. dry with materiala saturated brine and dried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled away
  6. customthe residue obtained
  7. customwas purified by silica gel chromatography (eluent; hexane-ethyl acetate=1:1)

Sources & evidence

ORD record
ord-d8ee0a7f7bae4922aa8ea54ca2e40ea9
Source dataset
uspto-grants-2002_04
Patent number
US06372800B1

Reaction notes

Loading…