Triethylamine → HCID 13136842, compound

Participants

Reaction Steps

To a solution of (cis)-4-(phenylthio)-L-proline (5 g) and triethylamine (3.4 g) in water (13 ml), a solution of 2-(t-butoxycarbonyloxyimino) 2-phenylacetonitrile (6.0 g) in dioxane (13 ml) is added. The mixture is stirred at ambient temperature. After one hour, water (50 ml) is added, the mixture is washed with ethyl acetate and acidified to a pH of 3-4 with 10% citric acid. The oil that separates is extracted into ethyl acetate, washed with brine, and dried (MgSO4). The residue is dissolved in saturated sodium bicarbonate (50 ml) plus water (600 ml). The alkaline solution is washed with ether and acidified to a pH of 4 with 10% citric acid. The oil that separates from solution is extracted into ethyl acetate, washed with brine, and dried (MgSO4). The solvent is removed in vacuo to give the product as an oil (5.9 g) that gradually solidifies, melting point 110°-118° C.

Provenance & Evidence