1,2-Dichloroethane → HCID 86690148, compound

HRID 2405660Notes

Reaction equation

HRID 2405660 reaction equation
[CH2:1]([NH:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[C:15](O)(=[O:23])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.S([O-])([O-])(=O)=O.[Mg+2]>C(Cl)Cl>[CH2:1]([N:9]([CH2:10][C:11]([O:13][CH3:14])=[O:12])[C:15](=[O:23])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

8

Reactant 6

HCID 111,2-DichloroethaneHCID 379Octanoic AcidHCID 24083Sulfuric acid magnesium salt (1:1)HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 43088882HCID 43088882, compound

Product 1

HCID 86690148HCID 86690148, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 2-(octylamino)acetate (31.6 mg, 0.157 mmol) and n-octanoic acid (30.0 μL, 0.188 mmol) were dissolved in 1 mL of well-dried DCM under argon condition and EDC (90.3 mg, 0.471 mmol), HOBt (63.6 mg, 0.471 mmol) and DIPEA (135 μL, 0.785 mmol) were added. The reaction mixture was then stirred for 12 hours at room temperature. Upon completion of the reaction, the reaction was terminated by adding 5 mL of water and the reaction mixture was extracted with DCM (4 mL×4). The organic layer thus obtained was treated with anhydrous magnesium sulfate to remove water. The precipitate was filtered out and the resulting solution was concentrated by distillation under reduced pressure and purified by column chromatography to obtain 44.7 mg (0.136 mmol, 87%) of the desired compound.

Workup

  1. additionwere added
  2. customUpon completion of the reaction
  3. customthe reaction was terminated
  4. additionby adding 5 mL of water
  5. extractionthe reaction mixture was extracted with DCM (4 mL×4)
  6. customThe organic layer thus obtained
  7. customto remove water
  8. filtrationThe precipitate was filtered out
  9. concentrationthe resulting solution was concentrated by distillation under reduced pressure
  10. custompurified by column chromatography

Sources & evidence

ORD record
ord-68b37185fb8e44489de1fdf5724c971d
Source dataset
uspto-grants-2014_08
Patent number
US08809012B2

Reaction notes

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