1,2-Dichloroethane → HCID 86690146, compound

HRID 2405654Notes

Reaction equation

HRID 2405654 reaction equation
[CH2:1]([C:4]1[CH:16]=[CH:15][C:7]([CH2:8][NH:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:6][CH:5]=1)[CH2:2][CH3:3].[CH2:17]([C:20]1[CH:25]=[CH:24][C:23]([CH2:26][C:27](O)=[O:28])=[CH:22][CH:21]=1)[CH2:18][CH3:19].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]([C:4]1[CH:16]=[CH:15][C:7]([CH2:8][N:9]([CH2:10][C:11]([O:13][CH3:14])=[O:12])[C:27](=[O:28])[CH2:26][C:23]2[CH:24]=[CH:25][C:20]([CH2:17][CH2:18][CH3:19])=[CH:21][CH:22]=2)=[CH:6][CH:5]=1)[CH2:2][CH3:3]

Participants

8

Reactant 6

HCID 111,2-DichloroethaneHCID 24083Sulfuric acid magnesium salt (1:1)HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 39362184-n-propylphenylacetic acidHCID 82677013HCID 82677013, compound

Product 1

HCID 86690146HCID 86690146, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 2-((4-propylbenzyl)amino)acetate (24.5 mg, 0.0983 mmol) and 2-(4-propylphenyl)acetic acid (17.5 mg, 0.0983 mmol) were dissolved in 1 mL of well-dried DCM under argon condition and then EDC (56.5 mg, 0.295 mmol), HOBt (39.8 mg, 0.295 mmol) and DIPEA (84.3 μL, 0.491 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 31.1 mg (0.0789 mmol, 80%) of the desired compound.

Workup

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

Sources & evidence

ORD record
ord-a5f5e9e4bbbc4d839dbc259802342dea
Source dataset
uspto-grants-2014_08
Patent number
US08809012B2

Reaction notes

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