1,2-Dichloroethane → HCID 2856855, compound

HRID 737099Notes

Reaction equation

HRID 737099 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.[C:11]1([CH:17]2[CH2:21][CH2:20][NH:19][CH2:18]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([N:19]2[CH2:20][CH2:21][CH:17]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:18]2)=[O:8])=[CH:9][CH:10]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 114644-Bromobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 31467433-Phenylpyrrolidine

Product 1

HCID 2856855HCID 2856855, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The above compound could be made in the following manner analogous to Example 60: 1 equivalent of p-Bromobenzoic acid, 1 equivalent 3-Phenylpyrrolidine, 1.1 equivalents of EDC, 1.1 equivalents of HOBt and 1 equivalent of Hunig's Base in DMF would be stirred at room temperature overnight. The solution would then be diluted with water and extracted with ethyl acetate. The organic layers would be combined and washed with water, aqueous saturated sodium bicarbonate solution, 1N HCl and brine. The organic layers would be dried with sodium sulfate, filtered and concentrated. Purification would be done with flash chromatography to afford product.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water, aqueous saturated sodium bicarbonate solution, 1N HCl and brine
  3. dry with materialThe organic layers would be dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification
  7. customto afford product

Sources & evidence

ORD record
ord-c26fcd04099e4d9da91d33e6d68f988b
Source dataset
uspto-grants-2009_09
Patent number
US07595397B2

Reaction notes

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