Hydrochloric Acid → N-[N-[15-methyl-3-(13-methyltetradecanoyloxy)hexadecanoyl]L-alanyl]-L-serine

HRID 1903535Notes

Reaction equation

HRID 1903535 reaction equation
[CH3:1][CH:2]([CH3:36])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]([O:19][C:20](=[O:35])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH:32]([CH3:34])[CH3:33])[CH2:15][C:16]([OH:18])=O.ON1C(=O)CCC1=O.FC(F)(F)C(O)=O.[NH2:52][C@H:53]([C:55]([NH:57][C@H:58]([C:61]([OH:63])=[O:62])[CH2:59][OH:60])=[O:56])[CH3:54].Cl>O1CCOCC1.CN(C)C=O.O.C(N(CC)CC)C>[CH3:36][CH:2]([CH3:1])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]([O:19][C:20](=[O:35])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH:32]([CH3:34])[CH3:33])[CH2:15][C:16]([NH:52][C@H:53]([C:55]([NH:57][C@H:58]([C:61]([OH:63])=[O:62])[CH2:59][OH:60])=[O:56])[CH3:54])=[O:18]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 80170N-HydroxysuccinimideHCID 2021675515-Methyl-3-(13-methyltetradecanoyloxy)hexadecanoic acidHCID 131713427HCID 131713427, compound

Product 1

HCID 86739313N-[N-[15-methyl-3-(13-methyltetradecanoyloxy)hexadecanoyl]L-alanyl]-L-serineYield 57.3%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 312751,4-DioxaneSolvent

Procedure

15-Methyl-3-(13-methyltetradecanoyloxy)hexadecanoic acid (80 mg) prepared by the method described in Preparation 1-(3) and N-hydroxysuccinimide (20 mg) were dissolved in dioxane (2 ml). N,N-Dicyclohexylcarbodiimide (37 mg) was added thereto under ice cooling. The mixture was reached to ambient temperature and stirred at the same temperature overnight. The crystallized urea was filtered off and the filtrate was concentrated to give a residue which was dissolved in N,N-dimethylformamide (3 ml). To the solution was added a solution of N-L-alanyl-L-serine trifluoroacetate (94 mg) and triethylamine (90 μl) in water (2 ml) at 0° C. The resulting mixture was reached to ambient temperature and stirred at the same temperature overnight. The reaction mixture was acidified with 1 N hydrochloric acid, extracted with ethyl acetate, washed with water and dried over magnesium sulfate. Ethyl acetate was distilled off to give a residue which was subjected to preparative thin layer chromatography (Merck, 0.25 mm×5) and eluted with a mixture of benzene, dioxane and acetic acid (10:5:1). The band containing the object compound was extracted with a mixture of methanol and chloroform (3:7) and the solvent was evaporated off under reduced pressure to afford a wax of N-[N-[15-methyl-3-(13-methyltetradecanoyloxy)hexadecanoyl]L-alanyl]-L-serine (60 mg).

Workup

  1. customdescribed in Preparation 1-(3)
  2. customwas reached to ambient temperature
  3. filtrationThe crystallized urea was filtered off
  4. concentrationthe filtrate was concentrated
  5. customto give a residue which
  6. customwas reached to ambient temperature
  7. stirringstirred at the same temperature overnight
  8. extractionextracted with ethyl acetate
  9. washwashed with water
  10. dry with materialdried over magnesium sulfate
  11. distillationEthyl acetate was distilled off
  12. customto give a residue which
  13. washeluted with a mixture of benzene, dioxane and acetic acid (10:5:1)
  14. additionThe band containing the object compound
  15. extractionwas extracted with a mixture of methanol and chloroform (3:7)
  16. customthe solvent was evaporated off under reduced pressure

Sources & evidence

ORD record
ord-a97fc37ec1544675a246f35af4fcf02e
Source dataset
uspto-grants-1984_03
Patent number
US04436726

Reaction notes

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