1,2-Dichloroethane → HCID 178476501, compound

HRID 1644869Notes

Reaction equation

HRID 1644869 reaction equation
[CH3:1][C:2]([C:20]1[CH:25]=[CH:24][C:23]([C:26](=[N:28]O)[NH2:27])=[CH:22][CH:21]=1)([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)=[CH:8][N:7]=1)[CH:3]([CH3:5])[CH3:4].[C:30]([O:33][CH2:34][C:35](O)=[O:36])(=[O:32])[CH3:31].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:30]([O:33][CH2:34][C:35](/[N:28]=[C:26](/[NH2:27])\[C:23]1[CH:22]=[CH:21][C:20]([C:2]([CH3:1])([C:6]2[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)=[CH:8][N:7]=2)[CH:3]([CH3:5])[CH3:4])=[CH:25][CH:24]=1)=[O:36])(=[O:32])[CH3:31]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 83766Acetoxyacetic acidHCID 516892Sodium BicarbonateHCID 76639029HCID 76639029, compound

Product 1

HCID 178476501HCID 178476501, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 3a (350 mg, 0.896 mmol) was added to a stirred solution of acetoxyacetic acid (126 mg, 1.07 mmol), EDC (205 mg, 1.07 mmol) and HOBt (157 mg, 1.16 mmol) in DCM (7.00 mL) at rt. After approximately 45 min, the reaction mixture was poured into saturated aqueous sodium bicarbonate and extracted three times with EtOAc. The combined organic extracts were washed with water, brine, dried (sodium sulfate) and concentrated in vacuo to afford the title compound 3b, which was used without further purification in the subsequent reaction. m/z (ES) 491 (MH)+.

Workup

  1. extractionextracted three times with EtOAc
  2. washThe combined organic extracts were washed with water, brine
  3. dry with materialdried (sodium sulfate)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-59ad282b6dfd406eaba779f5a7ad32ce
Source dataset
uspto-grants-2012_02
Patent number
US08124628B2

Reaction notes

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