Trifluoroacetic acid → 3-cyclohexyl-(L)-alanine phenylmethyl ester trifluoroacetate
Reaktionsgleichung
[C:1]1([CH2:7][O:8][C:9](=[O:26])[C@H:10]([CH2:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[NH:11]C(OC(C)(C)C)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:27][C:28]([F:33])([F:32])[C:29]([OH:31])=[O:30]>ClCCl>[F:27][C:28]([F:33])([F:32])[C:29]([OH:31])=[O:30].[C:1]1([CH2:7][O:8][C:9](=[O:26])[C@H:10]([CH2:19][CH:20]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]2)[NH2:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a stirred solution of 35.3 g (94.5 mmole) of N-[(1,1-dimethylethoxy)carbonyl]-3-cyclohexyl-(L)-alanine phenylmethyl ester in 100 mL of dichloromethane at 17° C. is added 100 mL of trifluoroacetic acid over 15 minutes during which time the reaction mixture temperature rises to 21° C. The reaction mixture is stirred overnight, then is concentrated in vacuo. The residue is azeotroped with dichloromethane, toluene and methyl tert-butyl ether. The resulting oil is subjected to high vacuum to afford 3-cyclohexyl-(L)-alanine phenylmethyl ester trifluoroacetate (32.6 g). MS (ion spray) m/z 262 (M+H)+.