Acetic Acid → HCID 68547352, compound

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[S:17][C:8]2[C:9]3[CH:10]=[CH:11][CH:12]=[C:13]([NH2:16])[C:14]=3[S:15][C:7]=2[C:6]=1[O:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[O:4].[C:25]1(=O)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.CC(O)=O>ClCCCl>[CH3:1][O:2][C:3]([C:5]1[S:17][C:8]2[C:9]3[CH:10]=[CH:11][CH:12]=[C:13]([NH:16][CH:25]4[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]4)[C:14]=3[S:15][C:7]=2[C:6]=1[O:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[O:4]

Participants

Procedure

Step A Reductive Amination: To a solution of 7-Amino-1-ethoxycarbonylmethoxy-3,8-dithia-cyclopenta[a]indene-2-carboxylic acid methyl ester (250 mg, 0.68 mmol) in DCE (6.5 mL) was added cyclohexanone (0.071 mL, 0.68 mmol), and NaBH3(OAc)3 (250 mg, 1.2 mmol). HOAc (0.05 mL, 0.82 mmol) was then added drop-wise and the solution was allowed to stir at ambient temperature for two hours after which the reaction was judged complete by TLC. The solution was filtered through silica gel, concentrated in vacuo and purified via normal phase SiO2 chromatography using a 0% to 15% ethyl acetate/hexane gradient, affording 180 mg of 7-Cyclohexylamino-1-ethoxycarbonylmethoxy-3,8-dithia-cyclopenta[a]indene-2-carboxylic acid methyl ester as a viscous yellow oil.