1,2-Dichloroethane → HCID 86754787, compound

HRID 322528Notes

Reaction equation

HRID 322528 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:13][C@@H:12]([CH3:14])[N:11](CC(O)=O)[C:10]1=[O:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.C1C=C[C:27]2[N:32](O)N=N[C:28]=2[CH:29]=1.CN1CC[O:38][CH2:37][CH2:36]1.[CH3:41][CH2:42][O:43][C:44]([CH3:46])=[O:45]>CC#N>[CH2:42]([O:43][C:44](=[O:45])[CH2:46][C@@H:27]([C:28]#[CH:29])[N:32]([N:11]1[C@H:12]([CH3:14])[CH2:13][C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C:10]1=[O:19])[C:37](=[O:38])[CH3:36])[CH3:41]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 8857Ethyl AcetateHCID 757711-HydroxybenzotriazoleHCID 22086393HCID 22086393, compound

Product 1

HCID 86754787HCID 86754787, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 13-9 (440 mg, 1.62 mmol), 2-9 (290 mg, 1.62 mmol), EDC (373 mg, 1.94 mmol), HOBT (262 mg, 1.94 mmol) and NMM (1.20 mL, 11.34 mmol) in CH3CN (5 mL) was stirred for 20 h. The mixture was diluted with EtOAc, washed with sat. NaHCO3, brine, and dried over MgSO4. Following evaporative removal of the solvent, the residue was chromatographed (silica gel, EtOAc) to give 13-10 as a colorless foam.

Workup

  1. washwashed with sat. NaHCO3, brine
  2. dry with materialdried over MgSO4
  3. customremoval of the solvent
  4. customthe residue was chromatographed (silica gel, EtOAc)

Sources & evidence

ORD record
ord-0c7d63223d0d4fb89a3924271aef5553
Source dataset
uspto-grants-2001_04
Patent number
US06211184B1

Reaction notes

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