Hydrochloric Acid → N-[N-(3-butanoyloxyhexanoyl)glycyl]-L-serine

HRID 1903531Notes

Reaction equation

HRID 1903531 reaction equation
[C:1]([O:6][CH:7]([CH2:12][CH2:13][CH3:14])[CH2:8][C:9]([OH:11])=O)(=[O:5])[CH2:2][CH2:3][CH3:4].ON1C(=O)CCC1=O.C1(N=C=NC2CCCCC2)CCCCC1.[NH2:38][CH2:39][C:40]([NH:42][C@H:43]([C:46]([OH:48])=[O:47])[CH2:44][OH:45])=[O:41].Cl>O1CCOCC1.CN(C)C=O.O.C(N(CC)CC)C>[C:1]([O:6][CH:7]([CH2:12][CH2:13][CH3:14])[CH2:8][C:9]([NH:38][CH2:39][C:40]([NH:42][C@H:43]([C:46]([OH:48])=[O:47])[CH2:44][OH:45])=[O:41])=[O:11])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 10868DicyclohexylcarbodiimideHCID 73086Serine, glycyl-HCID 80170N-HydroxysuccinimideHCID 204672993-Butanoyloxyhexanoic acid

Product 1

HCID 54092004N-[N-(3-butanoyloxyhexanoyl)glycyl]-L-serine

Reagents, catalysts & solvents 4

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

Procedure

3-Butanoyloxyhexanoic acid (234 mg) prepared by the method described in Preparation 6-(2) and N-hydroxysuccinimide (133 mg) was dissolved in dioxane (3 ml). N,N'-Dicyclohexylcarbodiimide (239 mg) was added thereto under ice cooling. The mixture was reached to room temperature and stirred at ambient temperature over night. The crystallized N,N'-dicyclohexyl 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 N-glycyl-L-serine (324 mg) and triethylamine (280 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 a mixture of methanol and chloroform (3:7) and the solvent was evaporated off under reduced pressure to afford a wax of N-[N-(3-butanoyloxyhexanoyl)glycyl]-L-serine.

Workup

  1. customdescribed in Preparation 6-(2)
  2. customwas reached to room temperature
  3. filtrationThe crystallized N,N'-dicyclohexyl 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 a mixture of methanol and chloroform (3:7)
  16. customthe solvent was evaporated off under reduced pressure

Sources & evidence

ORD record
ord-8aad065a2d9c4f4f86303b26759e09ed
Source dataset
uspto-grants-1984_03
Patent number
US04436726

Reaction notes

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