Dimethylformamide → HCID 178431719, compound

HRID 2047475Notes

Reaction equation

HRID 2047475 reaction equation
[CH3:1][C:2]([O:9][C:10](OC1C=CC([N+]([O-])=O)=CC=1)=[O:11])([CH3:8])[C:3](OCC)=[O:4].Cl.[NH2:23][C@H:24]1[CH2:29][CH2:28][C@H:27]([C:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:31])[CH2:26][CH2:25]1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[CH3:1][C:2]1([CH3:8])[O:9][C:10](=[O:11])[N:23]([C@H:24]2[CH2:29][CH2:28][C@H:27]([C:30]([O:32][CH2:33][C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)=[O:31])[CH2:26][CH2:25]2)[C:3]1=[O:4]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 67232782Ethyl 2-methyl-2-{[(4-nitrophenoxy)carbonyl]oxy}propanoateHCID 178479264HCID 178479264, compound

Product 1

HCID 178431719HCID 178431719, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of the compound (1.3 g) obtained in step 1, benzyl trans-4-aminocyclohexanecarboxylate monohydrochloride (1.1 g), potassium carbonate (0.88 g) and DMF (30 mL) was stirred at 60° C. for 6 hr. The mixture was diluted with water, and extracted with ethyl acetate. The extract was washed with water and saturated brine, dried and concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (solvent gradient; 0→25% ethyl acetate/hexane) to give benzyl trans-4-(5,5-dimethyl-2,4-dioxo-1,3-oxazolidin-3-yl)cyclohexanecarboxylate (1.2 g, 81%) as a white powder.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was separated
  6. custompurified by silica gel column chromatography (solvent gradient; 0→25% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-948fadc0160445599e6c171113a8f0c9
Source dataset
uspto-grants-2013_11
Patent number
US08592454B2

Reaction notes

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