Cyclohexylamine → 3-Benzyloxy-6-methyl-4-oxo-4H-pyran-2-carboxylic acid cyclohexylamide

HRID 420473Notes

Reaction equation

HRID 420473 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:13]([O:20][C:21]1[C:26](=[O:27])[CH:25]=[C:24]([CH3:28])[O:23][C:22]=1[C:29]([OH:31])=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH:32]1([NH2:38])[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1>CN(C)C=O>[CH:32]1([NH:38][C:29]([C:22]2[O:23][C:24]([CH3:28])=[CH:25][C:26](=[O:27])[C:21]=2[O:20][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[O:31])[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1

Participants

5

Reactant 3

HCID 7965CyclohexylamineHCID 682631,1'-CarbonyldiimidazoleHCID 98564973-(benzyloxy)-6-methyl-4-oxo-4H-pyran-2-carboxylic acid

Product 1

HCID 866117973-Benzyloxy-6-methyl-4-oxo-4H-pyran-2-carboxylic acid cyclohexylamideYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1,1′-carbonyldiimidazole (1.99 g, 12.30 mmol) was added to a solution of the 3-(benzyloxy)-6-methyl-4-oxo-4H-pyran-2-carboxylic acid (2.0 g, 7.69 mmol) in dimethylformamide (DMF, 18 ml) at room temperature. The resulting solution was heated at 40°-50° C. for 3 hrs. A light yellow solution was observed. Cyclohexylamine (1.23 ml, 10.76 mmol) was then added. The resulting mixture was stirred at room temperature for overnight. The DMF was removed under reduced pressure to give light yellow oil as a crude product, which was purified by flash column chromatography (elution gradient: from 1:1 ethyl acetate/hexane to 10% methanol in ethyl acetate) to yield the titled compound (1.60 g, yield 61%) as white solid.

Workup

  1. temperatureThe resulting solution was heated at 40°-50° C. for 3 hrs
  2. customThe DMF was removed under reduced pressure
  3. customto give light yellow oil as a crude product, which
  4. customwas purified by flash column chromatography (elution gradient: from 1:1 ethyl acetate/hexane to 10% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-1b89491ab49f4956a726c90df2609b3f
Source dataset
uspto-grants-2012_01
Patent number
US08097624B2

Reaction notes

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