Ethyl Acetate → HCID 54712198, compound

HRID 905900Notes

Reaction equation

HRID 905900 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:10]=2)[N:5]([CH3:16])[C:4](=[O:17])[C:3]=1[C:18](O)=[O:19].Cl.[CH2:22]([O:29][C:30](=[O:33])[CH2:31][NH2:32])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(C(C)C)CC)(C)C.CCOC(C)=O>CN(C=O)C.O.C(Cl)Cl>[CH2:22]([O:29][C:30](=[O:33])[CH2:31][NH:32][C:18]([C:3]1[C:4](=[O:17])[N:5]([CH3:16])[C:6]2[C:11]([C:2]=1[OH:1])=[CH:10][CH:9]=[C:8]([C:12]([O:14][CH3:15])=[O:13])[CH:7]=2)=[O:19])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 11701227Benzyl 2-aminoacetate hydrochlorideHCID 59340043HCID 59340043, compound

Product 1

HCID 54712198HCID 54712198, compoundYield 27.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

4-hydroxy-7-(methoxycarbonyl)-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (107 mg, 386 μmol), glycine benzyl ester hydrochloride (117 mg, 579 μmol), pybop (603 mg, 1158 μmol), and diisopropylethylamine (403 μl, 2316 μmol) were dissolved in DMF and stirred at room temperature for 24 hours. The reaction mixture was diluted with H2O and DCM, the layers were separated and the aqueous layer was extracted with DCM (3×), the organics were washed with H2O (2×) and dried over MgSO4, filtered and concentrated to yield a yellow solid. Flash column chromatography was performed using 2:1 Hex/EtOAc to give 45 mg of desired product.

Workup

  1. customthe layers were separated
  2. extractionthe aqueous layer was extracted with DCM (3×)
  3. washthe organics were washed with H2O (2×)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto yield a yellow solid

Sources & evidence

ORD record
ord-2e02215df8834cd08928829241350468
Source dataset
uspto-grants-2011_09
Patent number
US08012968B2

Reaction notes

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