Acetic Acid → 1-tert-Butoxycarbonyl-2(S)-(2-vinyloxyethyl)-4-naphthoylpiperazine

HRID 1598478Notes

Reaction equation

HRID 1598478 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][CH:17]=2)=[O:15])[CH2:10][C@@H:9]1[CH2:26][CH2:27][OH:28])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:29](O)(=O)[CH3:30]>C(OCC)=C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][CH:17]=2)=[O:15])[CH2:10][C@@H:9]1[CH2:26][CH2:27][O:28][CH:29]=[CH2:30])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 129668321-tert-Butoxycarbonyl-2(S)-(2-hydroxyethyl)-4-naphthoylpiperazine

Product 1

HCID 228841371-tert-Butoxycarbonyl-2(S)-(2-vinyloxyethyl)-4-naphthoylpiperazine

Reagents, catalysts & solvents 1

HCID 8023Ethyl vinyl etherSolvent

Procedure

1-tert-Butoxycarbonyl-2(S)-(2-hydroxyethyl)-4-naphthoylpiperazine (0.50 g, 1.3 mmol) was dissolved in freshly distilled ethyl vinyl ether (20 mL) under argon. To this solution was added mercuric acetate (0.436 g, 1.37 mmol) and the reaction refluxed overnight. The reaction was cooled to room temperature, acetic acid added (0.035 mL, 0.58 mmol) and stirred 2 h. The reaction mixture was extracted with ethyl acetate and 5% aqueous sodium hydroxide, and the organic phase further extracted with saturated sodium chloride solution and dried over magnesium sulfate. The crude product was chromatographed on silica gel with 30% ethyl acetate in hexane. The title compound was obtained as a white solid.

Workup

  1. temperaturethe reaction refluxed overnight
  2. extractionThe reaction mixture was extracted with ethyl acetate and 5% aqueous sodium hydroxide
  3. extractionthe organic phase further extracted with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customThe crude product was chromatographed on silica gel with 30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-3ac47fe6101d4888b514222b066163a6
Source dataset
uspto-grants-1998_04
Patent number
US05736539

Reaction notes

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