Diethyl Ether → Aconitic Acid

HRID 1648200

Reaktionsgleichung

Reaktionsgleichung von HRID 1648200
[CH2:1]([C:10]([OH:12])=[O:11])/[C:2](/[C:7]([OH:9])=[O:8])=[CH:3]\[C:4]([OH:6])=[O:5].C1N=CN(C(N2C=NC=C2)=O)C=1.FC(F)(F)S(O)(=O)=O.C1(SC)C=CC=CC=1.C1C(O)=CC=CC=1C.CCOCC>CN(C=O)C.FC(F)(F)C(O)=O.O>[C:10]([OH:12])(=[O:11])[CH:1]=[C:2]([CH2:3][C:4]([OH:6])=[O:5])[C:7]([OH:9])=[O:8]

Komponenten

8

Edukt 4

HCID 3283Diethyl EtherHCID 682631,1'-CarbonyldiimidazoleHCID 444212trans-Aconitic acidHCID 88261696Trifluoromethanesulfonic acid thioanisole m-cresol

Produkt 1

HCID 309Aconitic Acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 6422Trifluoroacetic acidLösungsmittel2×

Versuchsvorschrift

Trans-aconitic acid (0.17 g, 1.0 mmol) and trifluoroacetic acid salt of β-Ala--Arg(Mts)--Leu--Asp(OBn)--Ser(Bn)--NH--iPr (SEQ ID NO:11) (3.23 g, 3.0 mmol) were condensed with CDI in DMF. The product was treated as in Example 73 to obtain the objective compound in the protected form (0.67 g, 0.22 mmol). The protected compound was dissolved in trifluoroacetic acid (10 ml), added with a trifuluoroacetic acid solution of 1M-trifluoromethanesulfonic acid/thioanisole/m-cresol with ice cooling at 0° C. and allowed to react for 1 hour to eliminate the protective group on the side chains and at the terminal of the peptide. The reaction mixture was poured into ether, and resulted oily precipitate was dissolved in distilled water, washed with ethyl acetate, passed through an anion-exchange resin column (Amberlite IRA400; C1 form) to convert the product into hydrochloride and lyophilized to obtain the objective aconitic acid (β-Ala--Arg--Leu--Asp--Ser--NH--iPr)3 (SEQ ID NO:11)3 (0.29 g, 0.15 mmol).

Aufarbeitung

  1. additionThe product was treated as in Example 73
  2. customto obtain the objective compound in the protected form (0.67 g, 0.22 mmol)
  3. customto react for 1 hour
  4. customresulted oily precipitate
  5. washwashed with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-4b5f55f6c5894670ac2dba04d8ff9f08
Quelldatensatz
uspto-grants-1995_07
Patentnummer
US05436221

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