1,2-Dichloroethane → HCID 86690147, compound

HRID 2405657Notes

Reaction equation

HRID 2405657 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][NH:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:16]1([CH2:22][CH2:23][CH2:24][CH2:25][C:26](O)=[O:27])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.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>[C:16]1([CH2:22][CH2:23][CH2:24][CH2:25][C:26]([N:10]([CH2:11][C:12]([O:14][CH3:15])=[O:13])[CH2:9][CH2:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[O:27])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

8

Reactant 6

HCID 111,2-DichloroethaneHCID 16757Benzenepentanoic acidHCID 24083Sulfuric acid magnesium salt (1:1)HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 28567066HCID 28567066, compound

Product 1

HCID 86690147HCID 86690147, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 2-((3-phenylpropyl)amino)acetate (20.0 mg, 0.0965 mmol) and 5-phenylvaleric acid (22.0 mg, 0.116 mmol) were dissolved in 1 mL of well-dried DCM under argon condition, and EDC (55.5 mg, 0.289 mmol), HOBt (39.1 mg, 0.289 mmol) and DIPEA (82.7 μL, 0.482 mmol) were added and the reaction mixture was stirred for 20 hours at room temperature. Upon completion of the reaction, the reaction was terminated by adding 3 mL of water, and the reaction mixture was extracted with DCM (3 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 34.2 mg (0.0931 mmol, 96%) of the desired compound.

Workup

  1. additionwere added
  2. customUpon completion of the reaction
  3. customthe reaction was terminated
  4. additionby adding 3 mL of water
  5. extractionthe reaction mixture was extracted with DCM (3 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-4b1c276f721c41f686036a7666b79ae8
Source dataset
uspto-grants-2014_08
Patent number
US08809012B2

Reaction notes

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