Ethyl Acetate → HCID 136018654, compound

HRID 2053449Notes

Reaction equation

HRID 2053449 reaction equation
C([O:8][C:9](=O)[C:10]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=1[N:17]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:18](=[O:26])[CH2:19][C:20]1[O:24][N:23]=[C:22]([CH3:25])[CH:21]=1)C1C=CC=CC=1.[H-].[Na+].CCOC(C)=O>CN(C=O)C>[CH2:27]([N:17]1[C:11]2[C:10](=[CH:15][C:14]([Cl:16])=[CH:13][CH:12]=2)[C:9]([OH:8])=[C:19]([C:20]2[O:24][N:23]=[C:22]([CH3:25])[CH:21]=2)[C:18]1=[O:26])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 59655016HCID 59655016, compound

Product 1

HCID 136018654HCID 136018654, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2-{benzyl-[2-(3-methyl-isoxazol-5-yl)-acetyl]-amino}-5-chloro-benzoic acid benzyl ester (3.30 g, 7.58 mmol) in 25 ml of DMF at 0° C. was added NaH (340 mg). The mixture was stirred at rt for 1 h under Ar. Treated with 200 ml of EtOAc, the mixture was extracted with H2O (4×50 ml). The combined aqueous layers were neutralized to pH=6 with 1N HCl and extracted with EtOAc (4×50 ml). The combined org. layers were washed with H2O (2×50 ml), brine (50 ml) and dried (Na2SO4). Removal of the solvent under reduced pressure gave. 2.35 g (92%) of product as a white solid: 1H-NMR (CD3OD, 400 MHz) δ 9.49 (s, 1H), 8.21 (d, 1H, J=2.6 Hz), 7.48 (dd, 1H, J=9.0, 2.6 Hz), 7.17-7.36 (m, 7H), 5.60 (s, 2H), 2.43 (s, 3H), 2.54 (s, 3H). Mass spectrum (ESI, m/z): Calcd. for C20H15ClN203, 367.1 (M+H), found 367.0.

Workup

  1. extractionthe mixture was extracted with H2O (4×50 ml)
  2. extractionextracted with EtOAc (4×50 ml)
  3. washlayers were washed with H2O (2×50 ml), brine (50 ml)
  4. dry with materialdried (Na2SO4)
  5. customRemoval of the solvent under reduced pressure
  6. customgave

Sources & evidence

ORD record
ord-a8bfb03a37b5494da8c030525c3c8165
Source dataset
uspto-grants-2008_02
Patent number
US07326788B2

Reaction notes

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