Hydrochloric Acid → HCID 54090289, compound

HRID 1903534Notes

Reaction equation

HRID 1903534 reaction equation
[C:1]([O:18][CH:19]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH2:20][C:21]([OH:23])=O)(=[O:17])[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][CH3:16].ON1C(=O)CCC1=O.[NH2:47][CH2:48][CH2:49][C:50]([NH:52][C@H:53]([C:56]([OH:58])=[O:57])[CH2:54][OH:55])=[O:51].Cl>O1CCOCC1.CN(C)C=O.O.C(N(CC)CC)C>[C:1]([O:18][CH:19]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH2:20][C:21]([NH:47][CH2:48][CH2:49][C:50]([NH:52][C@H:53]([C:56]([OH:58])=[O:57])[CH2:54][OH:55])=[O:51])=[O:23])(=[O:17])[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][CH3:16]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 80170N-HydroxysuccinimideHCID 134890283-Hexadecanoyloxyoctadecanoic acidHCID 53912633HCID 53912633, compound

Product 1

HCID 54090289HCID 54090289, compoundYield 40.2%

Reagents, catalysts & solvents 4

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

Procedure

3-Hexadecanoyloxyoctadecanoic acid (150 mg) prepared by the method described in Preparation 2-(3) and N-hydroxysuccinimide (38 mg) were dissolved in dioxane (2 ml). N,N-Dicyclohexylcarbodiimide (68 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 (7 ml). To this solution was added a solution of N-β-alanyl-L-serine (100 mg) and triethylamine (100 μl) in water (4 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 powder of N-[N-(3-hexadecanoyloxyoctadecanoyl)-β-alanyl]-L-serine (78 mg).

Workup

  1. customdescribed in Preparation 2-(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-e4891f2797a04e029094bade1f4ada8f
Source dataset
uspto-grants-1984_03
Patent number
US04436726

Reaction notes

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