(S)-BENZYL 2-(TERT-BUTOXYCARBONYLAMINO)-2-(4-(TRIFLUOROMETHYLSULFONYLOXY)PHENYL)ACETATE synthesis
- Product Name:(S)-BENZYL 2-(TERT-BUTOXYCARBONYLAMINO)-2-(4-(TRIFLUOROMETHYLSULFONYLOXY)PHENYL)ACETATE
- CAS Number:176505-40-1
- Molecular formula:C21H22F3NO7S
- Molecular Weight:489.46
![Benzeneacetic acid, α-[[(1,1-dimethylethoxy)carbonyl]amino]-4-hydroxy-, phenylmethyl ester, (αS)-](/CAS/20210305/GIF/145794-17-8.gif)
Yield:176505-40-1 92%
Reaction Conditions:
with pyridine in dichloromethane at -15; for 0.0833333 h;
Steps:
45
To a mixture of phenylmethyl (2S)-2- [ (TERT-BUTOXY) CARBONYLAMINO]-2- (4-HYDROXYPHENYL) acetate (8.45g, 23. 6MMOL) in 22mL OF CH2C12 WHICH contained pyridine, (4.78mL, 59. 1MMOL) AT-15°C was added TRIFLUOROMETHANESULFONIC anhydride (4. 77mL, 28.4mmol). The mixture was stirred for 5 min, the reaction quenched with water and the mixture washed with 0. 5N NAOH (2 x 30ML), 15% citric acid (2 x 30ML) and brine. The organic layer was dried (Na2SO4), filtered, and concentrated to yield 10.60g (92%) of phenylmethyl (2S)-2-[(TERT-BUTOXY) CARBONYLAMINO]-2-{4-[(TRIFLUOROMETHYL) SULFONYLOXY] phenyl} acetate as light yellow solid. H NMR (300 MHz, CDC13) 6 7.43 (2H, d), 7.32-7. 16 (7H, m) 5.67 (1H, d), 5.40 (1H, d), 5.16 (2H, s), 1.43 (9H, s).
References:
WO2005/27856,2005,A2 Location in patent:Page/Page column 69
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