Reacción #1350601

Ecuación de reacción

water

(3S)-3-Amino-ε-caprolactam

triethylamine

Benzyl chloroformate

→

(S)-3-benzyloxycarbonylamino-ε-caprolactam

Rendimiento 39.4%

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   ExtracciónThe reaction mixture was extracted with ethyl acetate (3×100 ml)
2. 2
   SecadoThe combined extracts were dried (MgSO4)
3. 3
   Otroevaporated
4. 4
   OtroThe residue was triturated with ether (40 ml)
5. 5
   Filtraciónfiltered

Procedimiento

(3S)-3-Amino-ε-caprolactam (25 g) and triethylamine (19.7 g) were dissolved in THF (200 ml) and cooled to 5° C. Benzyl chloroformate (33 g) in THF (50ml) was added dropwise over 30 minutes. The reaction mixture was stirred at ambient temperature for 18 hours and then poured into water (500 ml). The reaction mixture was extracted with ethyl acetate (3×100 ml). The combined extracts were dried (MgSO4) and evaporated. The residue was triturated with ether (40 ml) and filtered to give 20 g of (S)-3-benzyloxycarbonylamino-ε-caprolactam as a white solid; NMR (d6-DMSO): 1.1-2(m, 6H), 2.9-3.2(m, 2H), 4.1-4.25 (m, 1H), 5.0 (s, 2H), 7.25-7.4 (m, 5H), 7.75 (t, 1H).

Fuente