Ammonia → (-)-Valerenic acid

HRID 2406862

Reaction equation

HRID 2406862 reaction equation
[CH3:1][C@H:2]1[C@@H:10]2[C:6](=[C:7]([CH3:11])[CH2:8][CH2:9]2)[C@H:5](/[CH:12]=[C:13](/[C:15]([OH:17])=[O:16])\[CH3:14])[CH2:4][CH2:3]1.C([N:20](CC)CC)C.ClC(OC)=O.N>C1COCC1>[CH3:1][C@H:2]1[C@@H:10]2[C:6](=[C:7]([CH3:11])[CH2:8][CH2:9]2)[C@H:5](/[CH:12]=[C:13](/[C:15]([OH:17])=[O:16])\[CH3:14])[CH2:4][CH2:3]1.[CH3:1][C@H:2]1[C@@H:10]2[C:6](=[C:7]([CH3:11])[CH2:8][CH2:9]2)[C@H:5](/[CH:12]=[C:13](/[C:15]([NH2:20])=[O:17])\[CH3:14])[CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 6440940(-)-Valerenic acid

Product 2

HCID 6440940(-)-Valerenic acidHCID 46835834HCID 46835834, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Valerenic acid (18.9 mg, 0.0807 mmol) was dissolved in THF (3 mL) and cooled to 0° C. Triethylamin (12.0 μL, 8.76 mg, 0.0866 mmol) and methyl chloroformate (97%, 8.5 μL, 9.36 mg, 0.0862 mmol) were added. After stirring for 1 hour the resulting solution was treated with aqueous ammonia (25% 25 μL, 5.5 mg, 0.3230 mmol). After 30 minutes the reaction mixture was warmed to room temperature and stirred for an additional hour. Then the mixture was filtrated and the filtrate concentrated in vacuo. Purification by chromatography (pure diethylether to diethylether/EtOAc 1/1) provided 6.6 mg Valerenic acid and 11.2 mg of Valerenic acid amide as white solid with 92% yield based on recovered starting material.

Workup

  1. temperatureAfter 30 minutes the reaction mixture was warmed to room temperature
  2. stirringstirred for an additional hour
  3. filtrationThen the mixture was filtrated
  4. concentrationthe filtrate concentrated in vacuo
  5. customPurification by chromatography (pure diethylether to diethylether/EtOAc 1/1)

Sources & evidence

ORD record
ord-f330f0febe7b45ef92818f4f1a40913a
Source dataset
uspto-grants-2014_08
Patent number
US08809395B2

Linked notes

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