Trifluoroacetic acid → (4S)-3-[3-(3-carboxy-4-methoxyphenyl)-2-ethylpropionyl]-4-benzyl-2-oxazolidinone

Reaktionsgleichung

C([O:8][C:9]([C:11]1[CH:12]=[C:13]([CH:19](O)[CH:20]([CH2:36][CH3:37])[C:21]([N:23]2[C@@H:27]([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:26][O:25][C:24]2=[O:35])=[O:22])[CH:14]=[CH:15][C:16]=1[O:17][CH3:18])=[O:10])C1C=CC=CC=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>>[C:9]([C:11]1[CH:12]=[C:13]([CH2:19][CH:20]([CH2:36][CH3:37])[C:21]([N:23]2[C@@H:27]([CH2:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH2:26][O:25][C:24]2=[O:35])=[O:22])[CH:14]=[CH:15][C:16]=1[O:17][CH3:18])([OH:10])=[O:8]

Komponenten

Edukt 3

HCID 6422Trifluoroacetic acid

HCID 12052Triethylsilane

HCID 69758110(4S)-3-[3-(3-benzyloxycarbonyl-4-methoxyphenyl)-2-ethyl-3-hydroxypropionyl]-4-benzyl-2-oxazolidinone

Produkt 1

HCID 69758575(4S)-3-[3-(3-carboxy-4-methoxyphenyl)-2-ethylpropionyl]-4-benzyl-2-oxazolidinoneAusbeute 124,8 %

Versuchsvorschrift

Next, (4S)-3-[3-(3-benzyloxycarbonyl-4-methoxyphenyl)-2-ethyl-3-hydroxypropionyl]-4-benzyl-2-oxazolidinone (1.35 g, 2.61 mmol) and 22 ml of trifluoroacetic acid were mixed under cooling with ice and triethylsilane (3.95 ml, 26.1 mmol) was added over 5 minutes. The mixture was stirred for 1 hour under cooling with ice, followed by stirring for 4 days at room temperature. The reaction mixture was concentrated and the residue was poured into 0.5 mol/l aqueous solution of sodium hydroxide, which was washed with ethyl acetate. The aqueous layer was made acidic and extracted with methylene chloride. The extract was washed with brine, then dried over anhydrous magnesium sulfate and concentrated to obtain 1.34 g of crude (4S)-3-[3-(3-carboxy-4-methoxyphenyl)-2-ethylpropionyl]-4-benzyl-2-oxazolidinone as a yellow oil. This compound was used for next reaction without purifying further.