1,2-Dichloroethane → Quinaldic Acid

HRID 1861627Notes

Reaction equation

HRID 1861627 reaction equation
NO.C(Cl)CCl.[CH:7]1[CH:8]=[CH:9][C:10]2N(O)N=[N:13][C:11]=2[CH:12]=1.C(N[C@H:25]([C:30]([OH:32])=[O:31])[CH2:26][CH:27](C)C)(OC(C)(C)C)=O>C(Cl)Cl.C(OCC)(=O)C>[N:13]1[C:11]2[C:10](=[CH:9][CH:8]=[CH:7][CH:12]=2)[CH:27]=[CH:26][C:25]=1[C:30]([OH:32])=[O:31]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 787HydroxylamineHCID 757711-HydroxybenzotriazoleHCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-

Product 1

HCID 7124Quinaldic AcidYield 212%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the amino alcohol of Example 1e (720 mg, 2.72 mmol) in CH2Cl2 was added EDC (521 mg), HOBt (368 mg) and N-Boc-leucine (630 mg). The reaction was maintained at room temperature until complete consumption of the starting material was observed by TLC analysis. The reaction was diluted with ethyl acetate and washed with 1N HCl, sat. K2CO3, water, brine, dried (MgSO4), filtered and concentrated. Column chromatography of the residue (3% methanol:dichloromethane) gave 1.0 g of the title compound: MS(EI) 478 (M+H+).

Workup

  1. washwashed with 1N HCl, sat. K2CO3, water, brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-919a03f0653d405698d146171c044bdb
Source dataset
uspto-grants-2003_03
Patent number
US06534498B1

Reaction notes

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