Methanol → HCID 44219374, compound

HRID 1486474Notes

Reaction equation

HRID 1486474 reaction equation
[C:1]([OH:20])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].N1C=CC=CC=1.CO.[NH:29]1[CH2:35][CH2:34][CH2:33][C@H:30]1[CH2:31][OH:32]>C(OCC)(=O)C>[C:1]([N:29]1[CH2:35][CH2:34][CH2:33][C@H:30]1[CH2:31][OH:32])(=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 5281Stearic AcidHCID 640091L-Prolinol

Product 1

HCID 44219374HCID 44219374, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of stearic acid (0.5 g 1.758 mmol) in 5 ml dry pyridine (kept over KOH) (0.399 g, 1.93 mmol) and NHS (0.223 g, 1.93 mmol) were added and dissolved in, stirred for 24 hr at room temperature. Reaction was followed by TLC 5% MeOH. Prolinol (0.197 g, 1.949 mmol) were added and the mixture was stirred at room temperature for three days was added to the mixture, and stirred at room temperature. Reaction controlled by TLC (100% Ethyl acetate). At the end of the reaction, volatiles were removed under reduced pressure and the mixture was dissolved in 30 ml DCM and DCU precipitate was filtrated off and the desired product was purified using column chromatography (ethyl acetate/DCM=1:1).

Workup

  1. dissolutiondissolved in,
  2. customReaction
  3. stirringthe mixture was stirred at room temperature for three days
  4. additionwas added to the mixture
  5. stirringstirred at room temperature
  6. customReaction
  7. customAt the end of the reaction, volatiles
  8. customwere removed under reduced pressure
  9. dissolutionthe mixture was dissolved in 30 ml DCM
  10. filtrationDCU precipitate was filtrated off
  11. customthe desired product was purified

Sources & evidence

ORD record
ord-bbdbc383681c4487bc4a6264d68885c0
Source dataset
uspto-grants-2016_08
Patent number
US09428448B2

Reaction notes

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