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

HRID 1903533Notes

Reaction equation

HRID 1903533 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.[NH2:45][CH2:46][CH2:47][C:48]([NH:50][C@H:51]([C:55]([OH:57])=[O:56])[C@@H:52]([CH3:54])[OH:53])=[O:49].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:45][CH2:46][CH2:47][C:48]([NH:50][C@H:51]([C:55]([OH:57])=[O:56])[C@@H:52]([CH3:54])[OH:53])=[O:49])=[O:18]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 80170N-HydroxysuccinimideHCID 18649800beta-alanyl-L-threonineHCID 2021675515-Methyl-3-(13-methyltetradecanoyloxy)hexadecanoic acid

Product 1

HCID 54090949N-[N-[15-methyl-3-(13-methyltetradecanoyloxy)hexadecanoyl]-beta-alanyl]-L-threonineYield 53.4%

Reagents, catalysts & solvents 4

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

Procedure

15-Methyl-3-(13-methyltetradecanoyloxy)hexadecanoic acid (140 mg) prepared by the method described in Preparation 1-(3) and N-hydroxysuccinimide (34 mg) were dissolved in dioxane (2.5 ml). N,N-Dicyclohexylcarbodiimide (63 mg) was added thereto under ice cooling. The mixture was reached to room temperature and stirred at ambient temperature overnight. The crystallized urea was filtered off and the filtrate was concentrated to give a residue which was dissolved in N,N-dimethylformamide (5 ml). To this solution was added a solution of β-alanyl-L-threonine (100 mg) and triethylamine (90 μl) in water (3 ml) at 0° C. The resulting mixture was reached to room temperature and stirred at ambient 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 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]-β-alanyl]-L-threonine (100 mg).

Workup

  1. customdescribed in Preparation 1-(3)
  2. customwas reached to room temperature
  3. filtrationThe crystallized urea was filtered off
  4. concentrationthe filtrate was concentrated
  5. customto give a residue which
  6. customwas reached to room temperature
  7. stirringstirred at ambient 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 methanol and chloroform (3:7)
  16. customthe solvent was evaporated off under reduced pressure

Sources & evidence

ORD record
ord-7a61bf282c84445c8e124e8cc94a18e6
Source dataset
uspto-grants-1984_03
Patent number
US04436726

Reaction notes

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