Cyclohexanone → HCID 69476031, compound

HRID 1034965Notes

Reaction equation

HRID 1034965 reaction equation
[CH2:1]([O:8][C:9](=[O:34])[N:10]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]2[CH:31]=[C:30]([NH2:32])[N:29]([CH3:33])[N:28]=2)[CH:22]=1)[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:35]1(=O)[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1>C(O)(=O)C>[CH2:1]([O:8][C:9](=[O:34])[N:10]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]2[C:31]([C:35]3[CH2:40][CH2:39][CH2:38][CH2:37][CH:36]=3)=[C:30]([NH2:32])[N:29]([CH3:33])[N:28]=2)[CH:22]=1)[CH2:11][C:12]1[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7967CyclohexanoneHCID 69475148HCID 69475148, compound

Product 1

HCID 69476031HCID 69476031, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of EXAMPLE 56D (4.5 g, 10 mmol) in acetic acid (100 mL) was treated with cyclohexanone (2 mL, 20 mmol) at ambient temperature for 4 days. The mixture was concentrated and the residue partitioned between dilute sodium hydroxide and ethyl acetate. The organic layer was washed with water and concentrated and the residue purified by flash chromatography on silica gel using ethyl acetate to give 3.8 g (71%) of the title compound. MS (DCI): m/z 537 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue partitioned between dilute sodium hydroxide and ethyl acetate
  3. washThe organic layer was washed with water
  4. concentrationconcentrated
  5. customthe residue purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-629a752661e0452da6f50d38c05b7e8b
Source dataset
uspto-grants-2013_10
Patent number
US08546368B2

Reaction notes

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