1,2-Dichloroethane → HCID 69121381, compound

HRID 1793786Notes

Reaction equation

HRID 1793786 reaction equation
[CH2:1]([CH:3]([CH2:7][CH3:8])[C:4]([OH:6])=O)[CH3:2].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.Cl.[CH2:24]([O:26][C:27]([C@@H:29]1[CH2:33][CH2:32][CH2:31][NH:30]1)=[O:28])[CH3:25].CN1CCOCC1>ClCCl>[CH2:24]([O:26][C:27]([C@@H:29]1[CH2:33][CH2:32][CH2:31][N:30]1[C:4](=[O:6])[CH:3]([CH2:1][CH3:2])[CH2:7][CH3:8])=[O:28])[CH3:25]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 69152-Ethylbutyric acidHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 11679912Ethyl L-prolinate hydrochloride

Product 1

HCID 69121381HCID 69121381, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To dichloromethane solution (350 ml) of 2-ethyl butanoic acid 5.68 g (48.9 mmol) under cooling on ice-water, HOBt 6.76 g (50 mmol), EDC 9.6 g (50 mmol) were added, stirring was continued for 30 min. 2(S)-pyrrolidine-carboxylic acid ethylester hydrochloride 8 g (45 mmol), NMM 4.55 g (45 mmol) were added to the reaction mixture and then stirred at room temperature for overnight. After then, the reaction mixture was washed with water, 1% sodium hydroxide solution, and then water sequentially. The organic layer was dried over sodium sulfate and the solvents were removed in vacuo. Purification by silica gel chromatography gave a desired product as an oil (8.16 g). NMR was consistent with the desired title product.

Workup

  1. additionwere added
  2. stirringstirred at room temperature for overnight
  3. washAfter then, the reaction mixture was washed with water, 1% sodium hydroxide solution
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customthe solvents were removed in vacuo
  6. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-7abcb2bf0aec4804aa52be0f83c4a4a0
Source dataset
uspto-grants-2006_04
Patent number
US07022677B1

Reaction notes

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