Acetic Acid → HCID 68547352, compound

HRID 2243500Notes

Reaction equation

HRID 2243500 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

5

Reactant 3

HCID 176Acetic AcidHCID 7967CyclohexanoneHCID 68543717HCID 68543717, compound

Product 1

HCID 68547352HCID 68547352, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

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.

Workup

  1. filtrationThe solution was filtered through silica gel
  2. concentrationconcentrated in vacuo
  3. custompurified via normal phase SiO2 chromatography

Sources & evidence

ORD record
ord-25eb40c349744f588dd45720adf278c1
Source dataset
uspto-grants-2010_03
Patent number
US07674822B2

Reaction notes

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