Zofenopril synthesis
- Product Name:Zofenopril
- CAS Number:81872-10-8
- Molecular formula:C22H23NO4S2
- Molecular Weight:429.55
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Yield:-
Reaction Conditions:
with water;sodium hydrogencarbonate;sodium carbonate in acetone; pH=8 - 10 at 15 - 20;Large scale reaction;
Steps:
3
General procedure: The (S)-amino acid (10.0 g) was dissolved in H2O (300 ml) and Na2CO3 (2.0 equiv) and NaHCO3 (1.0 equiv) were added at rt, with stirring, to give a clear solution. Acetone (4.0 vol, with respect to the amino acid) was added and the slightly turbid solution was cooled in an ice water bath to 15-20 °C. Cbz-Cl (1.25 equiv) was added slowly, with stirring, and the reaction mixture allowed to warm to rt. After stirring for an additional 3 h at rt the mixture was extracted with Et2O (50 ml). To the aqueous phase was slowly added aqueous HCl to give a pH of 2. The resulting oil was extracted into EtOAc (150 ml) and this was washed with H2O (100 ml) and then concentrated in vacuo to give the N-Cbz amino acid as a white solid, see Table 1.
References:
Pehere, Ashok D.;Abell, Andrew D. [Tetrahedron Letters,2011,vol. 52,# 13,p. 1493 - 1494] Location in patent:experimental part
