Hydrochloric Acid → HCID 131733893, compound

HRID 709330Notes

Reaction equation

HRID 709330 reaction equation
[NH2:1][C@H:2]([C:13]([OH:15])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[CH3:16][O-:17].[Na+].Cl.[OH-:20].[Na+].[CH2:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>CO.O>[NH:6]([C:5]([CH2:4][CH2:12][CH2:11][CH2:10][CH2:9][CH2:22][CH2:27][CH2:26][CH2:25][CH2:24][CH3:23])=[O:20])[C@H:7]([C:16]([NH:1][C@H:2]([C:13]([OH:15])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1)=[O:17])[CH3:8]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6305L-TryptophanHCID 8078CyclohexaneHCID 14798Sodium HydroxideHCID 10942334Sodium Methoxide

Product 1

HCID 131733893HCID 131733893, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A 100 mL four-neck flask was charged with 5.0 g (24.5 mmol) of L-tryptophan, 7.0 g (24.5 mmol) of N-lauroyl-Ala-methyl, 70 g of cyclohexane and 2.8 g of methanol, and the flask contents were stirred under heating at 60° C. on an oil bath. Next, 9.5 g (49.0 mmol) of a 28% methanol solution of sodium methoxide as the base was added, and stirring was continued for 2 hours at about 60° C. The oil bath was then removed, 1.4 g of methanol was added, and the solution was allowed to cool to 25° C. This solution was added, under stirring at 35° C., to a mixed solution composed of 84 g of water, 91 g of methanol and 8.2 mL (49.0 mmol) of 6N hydrochloric acid. The pH was set to 6.7 by adding a 0.1N aqueous sodium hydroxide solution, following which the solvent was driven off by concentration under reduced pressure. Ethyl acetate and water were added to the residue, and the aqueous phase was extracted with ethyl acetate. The aqueous phase was concentrated under a reduced pressure to drive off the water and effect drying, thereby giving 9.2 g (yield, 83%; purity, 99%) of white crystals of free form of N-lauroyl-Ala-Trp.

Workup

  1. stirringstirring
  2. customThe oil bath was then removed
  3. addition1.4 g of methanol was added
  4. temperatureto cool to 25° C
  5. additionThis solution was added
  6. stirringunder stirring at 35° C., to a mixed solution
  7. concentrationwas driven off by concentration under reduced pressure
  8. additionEthyl acetate and water were added to the residue
  9. extractionthe aqueous phase was extracted with ethyl acetate
  10. concentrationThe aqueous phase was concentrated under a reduced pressure
  11. customdrying
  12. customgiving

Sources & evidence

ORD record
ord-cc3b761693764cffba9016ba0f41ae22
Source dataset
uspto-grants-2015_11
Patent number
US09180201B2

Reaction notes

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