Hydrochloric Acid → Ceramide NG

Participants

Reaction Conditions

Reaction Steps

Ethyl (2R,3R)-2-octadecanoylamino-3-hydroxyoctadecanoate (5.00 g, 8.17 mmol) synthesized in the same manner as Example 17 was added to a THF suspension (48 mL) containing sodium borohydride (0.62 mg, 16.34 mmol) at 0° C. for 5 hour. After completion of the dropwise addition, calcium chloride (1.82 mg, 16.40 mmol) was added for 1 hour. After water was added to the reaction mixture, concentrated hydrochloric acid was added thereto to adjust pH of the mixture to be 1.5. The mixture was further stirred at 50° C. for 1 hour, and the organic layer was separated. It was confirmed by comparative analysis of the organic layer with sample product using HPLC that the organic layer contained 4.41 g of the title compound (yield: 95%). It was also found that anti-form:syn-form was 98:2 and the optical purity of the anti-form was 99% ee.

Provenance & Evidence