5-cyanobenzofuran-2-carboxylic Acid → t-Butyl 3-[4-[(5-cyano-2-benzofuranyl)carbonylamino]cyclohexyl]propionate

HRID 1290991Notes

Reaction equation

HRID 1290991 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]([OH:13])=O)=[CH:8][C:7]=2[CH:14]=1)#[N:2].[NH2:15][CH:16]1[CH2:21][CH2:20][CH:19]([CH2:22][CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:18][CH2:17]1>>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]([NH:15][CH:16]3[CH2:17][CH2:18][CH:19]([CH2:22][CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:21]3)=[O:13])=[CH:8][C:7]=2[CH:14]=1)#[N:2]

Participants

3

Reactant 2

HCID 102360545-cyanobenzofuran-2-carboxylic AcidHCID 18919405HCID 18919405, compound

Product 1

HCID 18919447t-Butyl 3-[4-[(5-cyano-2-benzofuranyl)carbonylamino]cyclohexyl]propionateYield 38.5%

Procedure

In the same manner as in Example 1 (2), 5-cyano-2-benzofurancarboxylic acid (203 mg, 1.08 mmol) and t-butyl 3-(4-aminocyclohexyl)propionate (295 mg, 1.30 mmol) were condensed and purified by silica gel column chromatography (n-hexane/ethyl acetate=2/1) to give 165 mg of t-butyl 3-[4-[(5-cyano-2-benzofuranyl)carbonylamino]cyclohexyl]propionate as a colorless solid (38%).

Workup

  1. customcondensed
  2. custompurified by silica gel column chromatography (n-hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-832c2b7e31934dcda9c3ffec5420e5d6
Source dataset
uspto-grants-1998_05
Patent number
US05753670

Reaction notes

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