1,2-Dichloroethane → HCID 86754781, compound

HRID 1602624Notes

Reaction equation

HRID 1602624 reaction equation
[C:1]([OH:4])(=[O:3])C.[CH2:5](Cl)[CH2:6]Cl.[CH:9]1[CH:10]=[CH:11][C:12]2N(O)N=[N:15][C:13]=2C=1.CN1CC[O:23][CH2:22][CH2:21]1.[CH3:26][C:27]#[N:28]>C(OCC)(=O)C.CN(C=O)C>[CH2:5]([O:4][C:1](=[O:3])[CH2:26][C@@H:27]([C:12]1[CH:13]=[N:15][CH:9]=[CH:10][CH:11]=1)[NH:28][C:22](=[O:23])[CH3:21])[CH3:6]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 176Acetic AcidHCID 6342AcetonitrileHCID 79724-MethylmorpholineHCID 757711-Hydroxybenzotriazole

Product 1

HCID 86754781HCID 86754781, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-11 (0.30 g, 0.882 mmol), 2-10 (0.354 g, 1.32 mmol), EDC (0.220 g (1.15 mmol), HOBT (0.143 g, 1.05 mmol) and NMM (0.680 mL (6.18 mmol) in CH3CN (5 mL) and DMF (3 mL) at 0° C. was stirred for 10 min, then allowed to warm and stir for 20 h. The mixture was diluted with ethyl acetate, washed with water, brine, and dried over sodium sulfate. Following evaporative removal of the solvent, the residue was chromatographed (silica gel, 70:20:10 chloroform/ethyl acetate/MeOH to give 3-14 as a colorless foam.

Workup

  1. temperatureto warm
  2. washwashed with water, brine
  3. dry with materialdried over sodium sulfate
  4. customremoval of the solvent
  5. customthe residue was chromatographed (silica gel, 70:20:10 chloroform/ethyl acetate/MeOH

Sources & evidence

ORD record
ord-9e920959b10844f9bf7e46bb7fd88bef
Source dataset
uspto-grants-1999_11
Patent number
US05981546

Reaction notes

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