Reacción #2195509

Ecuación de reacción

Water

Triethylamine

Methyl (4S)-4-hydroxyprolinate

3-cyanobenzenesulfonyl chloride

→

desired product

Rendimiento 78.1%

Methyl (4S)-1-[(3-Cyanophenyl)sulfonyl]-4-hydroxyprolinate

Rendimiento 78.1%

Disolventes

—

hexanes

Ethyl acetate

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónthe aqueous layer was extracted three times with CH2Cl2
2. 2
   LavadoThe combined organic layers were washed with 1N HCl, H2O, 1N NaOH, and brine
3. 3
   Secadodried over MgSO4
4. 4
   Concentraciónconcentrated
5. 5
   Otroto give a viscous residue
6. 6
   workup.DISSOLUTIONto completely dissolve the residue
7. 7
   workup.STIRRINGThe mixture was then stirred overnight
8. 8
   Otroto precipitate
9. 9
   FiltraciónThe solid was filtered
10. 10
    Lavadorinsed two times with 30% EtOAc/hexanes

Procedimiento

Methyl (4S)-4-hydroxyprolinate (52.0 g, 0.286 mol) was dissolved in 500 mL CH2Cl2 and cooled to 0° C. Triethylamine (83.6 mL, 0.600 mol) was added, followed by 3-cyanobenzenesulfonyl chloride (55.0, 0.273 mol) slowly. The reaction mixture was stirred at room temperature overnight. Water was added, and the aqueous layer was extracted three times with CH2Cl2. The combined organic layers were washed with 1N HCl, H2O, 1N NaOH, and brine, dried over MgSO4, and concentrated to give a viscous residue. Ethyl acetate (300 mL) was added to completely dissolve the residue. Approximately 100 mL hexanes was added slowly until the solution became slightly cloudy. The mixture was then stirred overnight to allow the product to precipitate. The solid was filtered and rinsed two times with 30% EtOAc/hexanes to give the desired product as an off-white powder (66.2 g, 78%). 1H-NMR (CDCl3, 500 MHz) δ 8.20-8.18 (m, 1H), 8.15-8.12 (m, 1H), 7.92-7.89 (m, 1H), 7.72 (t, 1H), 4.51-4.47 (m, 1H), 4.42 (br s, 1H), 3.74 (s, 3H), 3.53-3.49 (m, 1H), 3.46-3.43 (m, 1H), 3.39 (br s, 1H), 2.29-2.25 (m, 1H), 2.21-2.02 (m, 1H). MS (ESI) calculated for C13H14N2O5S 310.3, observed m/e 311.2 (MH+).

Fuente