تفاعل #169957

معادلة التفاعل

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

المردود 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

المردود 74.1%

المذيبات

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   تركيزThe mixture was concentrated under reduced pressure
2. 2
   workup.ADDITIONdiluted with saturated NaHCO3
3. 3
   استخلاصextracted with EtOAc
4. 4
   غسيلThe organic layer was washed with brine
5. 5
   تجفيفdried with MgSO4
6. 6
   ترشيحfiltered
7. 7
   تركيزconcentrated under reduced pressure
8. 8
   أخرىPurification
9. 9
   غسيلby chromatography (SiO2, eluted with CH2Cl2-MeOH: 6:1)

الإجراء التجريبي

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.

المصدر