Sodium Carbonate → HCID 53708079, compound

HRID 1600570Notes

Reaction equation

HRID 1600570 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:18][N:17]=[CH:16][CH:15]=2)=[CH:10][CH:9]=1)[NH2:6])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].[CH3:26][C:27]1[CH:28]=[C:29]([CH:33]=[C:34]([CH3:36])[CH:35]=1)[C:30](Cl)=[O:31].CCCCCC.C(OCC)(=O)C>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4](=[O:19])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:18][N:17]=[CH:16][CH:15]=2)=[CH:10][CH:9]=1)[NH:6][C:30](=[O:31])[C:29]1[CH:33]=[C:34]([CH3:36])[CH:35]=[C:27]([CH3:26])[CH:28]=1)[CH3:2]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 810883,5-Dimethylbenzoyl ChlorideHCID 21226206Ethyl acetate hexaneHCID 54136862HCID 54136862, compound

Product 1

HCID 53708079HCID 53708079, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
10 °C

Procedure

Crude 3-[4-(5-isoxazolyl)-phenyl]-alanine ethyl ester (660 mg) is dissolved in chloroform (6.6 ml), stirred vigorously with 2N aqueous sodium carbonate (1.4 ml), and after cooling to 10° C., 3,5-dimethylbenzoylchloride (0.7 ml) is added. Stirring is continued for 1 hour at 10° C. and for 2 hours at ambient temperature. Then extraction with di chloromethane/water, washing with 10% aqueous citric acid, and with brine, followed by evaporation gives the crude product. Flash chromatography on silica gel, hexane/ethyl acetate (4:1), gives pure N-(3,5-dimethylbenzoyl)-3-[4-(5-isoxazolyl)-phenyl]-alanine ethyl ester.

Workup

  1. extractionThen extraction with di chloromethane/water
  2. washwashing with 10% aqueous citric acid
  3. customwith brine, followed by evaporation
  4. customgives the crude product

Sources & evidence

ORD record
ord-f83b10e262d9406c83b3fde5c02b2be2
Source dataset
uspto-grants-1999_11
Patent number
US05977075

Reaction notes

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