Formic Acid → HCID 86638486, compound

Reaction equation

C(N(CC)CC)C.C(O)=O.[C:11]([NH:14][CH:15]([C:21](=[O:37])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[C:16]([O:18][CH2:19][CH3:20])=[O:17])(=[O:13])[CH3:12]>C1COCC1>[C:11]([NH:14][C@H:15]([C@H:21]([OH:37])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[C:16]([O:18][CH2:19][CH3:20])=[O:17])(=[O:13])[CH3:12]

Participants

Procedure

A dehydrated THF solution (0.5 ml) of triethylamine (131.9 mg, 1.30 mmol) and a dehydrated THF solution (0.5 ml) of formic acid (64.2 mg, 1.37 mmol) were added to a dehydrated THF solution (4.0 ml) of RuCl[(R,R)-TsDPEN](p-cymene) complex (19.6 mg, 0.03 mmol) and ethyl 2-acetylamino-3-oxooctadecanoate (7.70 g, 0.20 mmol) synthesized in the same method as Example 1. After the mixture was stirred for 3 days at room temperature, the reaction solvent was removed in reduced pressure. Water was added thereto, and the mixture was extracted with ethyl acetate three times. The organic layers were combined and dried with magnesium sulfate. After the solvent was removed in reduced pressure, the obtained crude product was purified by silica gel chromatography (Kieselgel 60 manufactured by Merck, solely ethyl acetate) to obtain the title compound (71.3 mg, yield: 94%). The product was analyzed by HPLC to find that anti-form:syn-form was 93:7 and the optical purity of the anti-form was 98% ee.