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Potassium Carbonate → HCID 10648237, compound

HRID 617576
Notes
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Reaction equation

HRID 617576 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-d12ec3c6697d420eac1cdf6f86d77001
Source dataset
uspto-grants-1999_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05948820

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes