Acetic Acid → HCID 54579141, Verbindung
Reaktionsgleichung
[CH2:1]([C:3]1[C:8]([CH2:9][CH:10]=O)=[CH:7][CH:6]=[CH:5][C:4]=1[C:12]1[S:16][C:15]([C:17]2[CH:18]=[CH:19][C:20]([O:25][CH:26]([CH3:28])[CH3:27])=[C:21]([CH:24]=2)[C:22]#[N:23])=[N:14][CH:13]=1)[CH3:2].[NH:29]1[CH2:36][CH2:35][CH2:34][C@H:30]1[C:31]([OH:33])=[O:32].C(O)(=O)C.C([BH3-])#N.[Na+]>>[C:22]([C:21]1[CH:24]=[C:17]([C:15]2[S:16][C:12]([C:4]3[C:3]([CH2:1][CH3:2])=[C:8]([CH2:9][CH2:10][N:29]4[CH2:36][CH2:35][CH2:34][C@H:30]4[C:31]([OH:33])=[O:32])[CH:7]=[CH:6][CH:5]=3)=[CH:13][N:14]=2)[CH:18]=[CH:19][C:20]=1[O:25][CH:26]([CH3:28])[CH3:27])#[N:23]Komponenten
5
Versuchsvorschrift
A solution of 5-{5-[2-ethyl-3-(2-oxoethyl)phenyl]-1,3-thiazol-2-yl}-2-[(1-methylethyl) oxy]benzonitrile (D76) (60 mg, 0.154 mmol), L-proline (35.4 mg, 0.307 mmol) and acetic acid (0.1 ml, 1.747 mmol) was stirred at room temperature for 15 min, then sodium cyanoborohydride (29.0 mg, 0.461 mmol) was added. The mixture was stirred at room temperature for 2 h. After concentration, the residue was partitioned between ethyl acetate and aqueous HCl (2M). The organic phase was washed with saturated brine, concentrated and purified by Mass Directed AutoPrep to afford 1-{2-[3-(2-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,3-thiazol-5-yl)-2-ethylphenyl]ethyl}-L-proline (E88) (11 mg) as a TFA salt.
Aufarbeitung
- concentrationAfter concentration
- customthe residue was partitioned between ethyl acetate and aqueous HCl (2M)
- washThe organic phase was washed with saturated brine
- concentrationconcentrated
- custompurified by Mass Directed AutoPrep
Quellen und Nachweise
- ORD-Eintrag
- ord-ba22592596b44926b86d2087ee639e5c
- Quelldatensatz
- uspto-grants-2013_03
- Patentnummer
- US08389508B2
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