ChemicalBook CAS DataBase List OLVANIL

OLVANIL synthesis

7synthesis methods

Product Name:OLVANIL
CAS Number:58493-49-5
Molecular formula:C26H43NO3
Molecular Weight:417.62

112-77-6
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$21.00/1g

1196-92-5
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$544.00/500g

58493-49-5
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$41.00/5mg

Yield: 89%

Reaction Conditions:

with triethylamine in N,N-dimethyl-formamide at 20; for 5 h;Cooling with ice;

Steps:

General Procedure for Preparation of N-Acylhistamines (N-Acyl-HAs)
General procedure: A solution of fatty acid acyl chloride (1.0 mmol), purchased from Tokyo Chemical Industory (Tokyo, Japan), in N,N-dimethylformamide (DMF) (2 mL) was added dropwise to a suspension of histamine dihydrochlolide (2.0 mmol) and Et₃N (8 mmol) in DMF (5 mL) cooled in an ice bath. In some cases (i.e., for the C18:1, C18:2 and C20:4 analogues), the acyl chlorides were prepared by reacting the free fatty acids with oxalyl chloride (5 eq, CH₂Cl₂, r.t., 3 h). The reaction mixture was stirred for 5 h at room temperature. Ice water was added to the mixture and the reaction mix was extracted with CHCl₃. The organic layer was dried over Na₂SO₄and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (CHCl₃ : MeOH : aq. NH₃=20 : 1 : 0.5) to give the corresponding N-acylhistamine.

References:

Takao, Koichi;Noguchi, Kaori;Hashimoto, Yosuke;Shirahata, Akira;Sugita, Yoshiaki [Chemical and Pharmaceutical Bulletin,2015,vol. 63,# 4,p. 278 - 285]

1196-92-5
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$544.00/500g

112-80-1 Synthesis