Reaktion #169957

Reaktionsgleichung

solution

tert-butyl (1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-{[2-({[(2Z)-5-tert-butyl-3-[(2R)-tetrahydrofuran-2-ylmethyl]-1,3-thiazol-2(3H)-ylidene]amino}carbonyl)-4-(trifluoromethyl)phenoxy]methyl}ethylcarbamate

trifluoroacetic acid

→

title compound

Ausbeute 74.1%

2-{[(2R)-2-amino-3-hydroxypropyl]oxy}-N-[(2Z)-5-tert-butyl-3-[(2R)-tetrahydrofuran-2-ylmethyl]-1,3-thiazol-2(3H)-ylidene]-5-(trifluoromethyl)benzamide

Ausbeute 74.1%

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe mixture was concentrated under reduced pressure
2. 2
   workup.ADDITIONdiluted with saturated NaHCO3
3. 3
   Extraktionextracted with EtOAc
4. 4
   WaschenThe organic layer was washed with brine
5. 5
   Trocknendried with MgSO4
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated under reduced pressure
8. 8
   SonstigePurification
9. 9
   Waschenby chromatography (SiO2, eluted with CH2Cl2-MeOH: 6:1)

Vorschrift

A solution of Example 69A (500 mg, 0.7 mmol) in CH2Cl2 (10 mL) at 0° C. was treated with trifluoroacetic acid (0.27 mL, 3.5 mmol). The mixture was allowed to warm to room temperature and stirred for 3 hours. The mixture was concentrated under reduced pressure, diluted with saturated NaHCO3 and extracted with EtOAc. The organic layer was washed with brine, dried with MgSO4, filtered, and concentrated under reduced pressure. Purification by chromatography (SiO2, eluted with CH2Cl2-MeOH: 6:1) afforded 260 mg of the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.33 (s, 9 H), 1.58-1.73 (m, 1H), 1.75-2.04 (m, 3 H), 2.25-2.43 (m, 1 H), 3.08 (q, J=5.6 Hz, 1 H), 3.36-3.53 (m, 3 H), 3.59-3.69 (m, 1 H), 3.74-3.86 (m, 1 H), 3.94-4.01 (m, 1 H), 4.05-4.12 (m, 1 H), 4.19-4.36 (m, 3 H), 4.68 (t, J=5.2 Hz, 1 H), 7.24-7.34 (m, 2 H), 7.76 (dd, J=8.9, 2.2 Hz, 1 H), 8.07 (d, J=2.4 Hz, 1 H); MS (DCI/NH3) m/z 502 (M+H)+. Anal calculated for C23H30F3N3O4S.0.75H2O: C, 53.63; H, 6.16; N, 8.16. Found: C, 53.40; H, 6.06; N, 8.16.

Quelle