Triethylamine → HCID 69026834, compound

HRID 1867197Notes

Reaction equation

HRID 1867197 reaction equation
[CH3:1][CH:2](/[CH:4]=[CH:5]/[CH2:6][CH2:7][CH2:8][CH2:9][C:10]([NH:12][CH2:13][C:14]1[CH:15]=[CH:16][C:17]([OH:22])=[C:18]([O:20][CH3:21])[CH:19]=1)=[O:11])[CH3:3].ClC([O:26][CH:27]1[CH:32]([CH:33]([CH3:35])[CH3:34])[CH2:31][CH2:30][CH:29]([CH3:36])[CH2:28]1)=O.C(N(CC)CC)C>ClCCl>[CH3:3][CH:2](/[CH:4]=[CH:5]/[CH2:6][CH2:7][CH2:8][CH2:9][C:10]([NH:12][CH2:13][C:14]1[CH:15]=[CH:16][C:17]([OH:22])=[C:18]([O:20][CH3:21])[CH:19]=1)=[O:11])[CH3:1].[CH3:36][C@H:29]1[CH2:28][C@@H:27]([OH:26])[C@H:32]([CH:33]([CH3:35])[CH3:34])[CH2:31][CH2:30]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 151928Menthyl chloroformateHCID 1548943Capsaicin

Product 1

HCID 69026834HCID 69026834, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of capsaicin (0.7 g, 2.3 mmol) and (−)-menthyl chloroformate (0.5 g, 2.3 mmol) in anhydrous dichloromethane (10 mL) was added triethylamine (0.45 g, 4.5 mmol) dropwise at ambient temperature. After the addition, the reaction mixture was stirred at ambient temperature for 2 hours. The reaction mixture was diluted with dichloromethane (DCM), washed with 5% aqueous K2CO3 solution, brine, dried over MgSO4, concentrated to dryness. The obtained crude product was purified through silica gel column chromatography (30% -50% ethyl acetate in hexane as the eluent) to give 0.98 g of capsaicin l-menthol mutual prodrug (87% yield) as clear viscous oil. 1H-NMR and 13C-NMR of the obtained capsaicin l-menthol mutual prodrug were consistent with the desired structure (see FIGS. 34, 35). Mass spectral analysis of the product was consistent with the desired structure (FIG. 36).

Workup

  1. additionAfter the addition
  2. washwashed with 5% aqueous K2CO3 solution, brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated to dryness
  5. customThe obtained crude product
  6. customwas purified through silica gel column chromatography (30% -50% ethyl acetate in hexane as the eluent)

Sources & evidence

ORD record
ord-857775146b6040068948259e4f7c9b60
Source dataset
uspto-grants-2009_12
Patent number
US07632519B2

Reaction notes

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