Hydrochloric Acid → HCID 131733892, compound

HRID 709329Notes

Reaction equation

HRID 709329 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.[CH2:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.[CH3:22][O-:23].[Na+].Cl.[OH2:26]>CO>[NH:6]([C:7]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:4][CH2:3][CH2:2][CH2:13][CH2:16][CH2:21][CH2:20][CH2:19][CH2:18][CH3:17])=[O:26])[CH2:5][C:22]([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:23]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 6305L-TryptophanHCID 8078CyclohexaneHCID 10942334Sodium Methoxide

Product 1

HCID 131733892HCID 131733892, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Conditions

Temperature
60 °C

Procedure

A 100 mL four-neck flask was charged with 1.25 g (6.1 mmol) of L-tryptophan, 2.0 g (6.1 mmol) of N-palmitoyl-Gly-methyl, 20 g of cyclohexane and 0.8 g of methanol, and stirred under heating at 60° C. on an oil bath. Next, 2.4 g (12.2 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, 0.4 g of methanol was added and, after being allowed to cool to 25° C., this solution was added, at 25° C. and under stirring, to a mixed solution composed of 30 g of water, 40 g of methanol and 2.0 mL (12.2 mmol) of 6N hydrochloric acid. After addition of the entire amount had been completed, the reaction solution was heated to 60° C. and stirred for 1 hour. The solution was then allowed to cool to 25° C. and the solid that deposited out was collected by filtration and washed with 6 g of water. Next, 30 g of water and 40 g of methanol were added to the resulting solid, and the system was heated to 60° C. and stirred for 1 hour. The system was then allowed to cool to 25° C. and the solid that deposited out was collected by filtration and washed with 6 g of water. The resulting solid was dried under reduced pressure, thereby giving 2.3 g (yield, 74%; purity, 90%) of white crystals of free form of N-palmitoyl-Gly-Trp.

Workup

  1. stirringstirring
  2. customThe oil bath was then removed
  3. addition0.4 g of methanol was added
  4. temperatureto cool to 25° C.
  5. additionthis solution was added, at 25° C.
  6. stirringunder stirring, to a mixed solution
  7. additionAfter addition of the entire amount
  8. temperaturethe reaction solution was heated to 60° C.
  9. stirringstirred for 1 hour
  10. temperatureto cool to 25° C.
  11. filtrationthe solid that deposited out was collected by filtration
  12. washwashed with 6 g of water
  13. additionNext, 30 g of water and 40 g of methanol were added to the resulting solid
  14. temperaturethe system was heated to 60° C.
  15. stirringstirred for 1 hour
  16. temperatureto cool to 25° C.
  17. filtrationthe solid that deposited out was collected by filtration
  18. washwashed with 6 g of water
  19. customThe resulting solid was dried under reduced pressure
  20. customgiving

Sources & evidence

ORD record
ord-83232adb488e4ce795eabf39986a178e
Source dataset
uspto-grants-2015_11
Patent number
US09180201B2

Reaction notes

Loading…