Hydrochloric Acid → HCID 136386265, compound

HRID 389933Notes

Reaction equation

HRID 389933 reaction equation
[BH4-].[Na+].[CH2:3]([NH:5][C:6]([C:8]1[C:12]([NH:13][CH2:14][C:15]2[O:19][N:18]=[C:17]([C:20](OC)=[O:21])[CH:16]=2)=[C:11]([C:24]2[CH:29]=[C:28]([Cl:30])[C:27]([OH:31])=[CH:26][C:25]=2[OH:32])[O:10][N:9]=1)=[O:7])[CH3:4].Cl>CCO.O>[OH:21][CH2:20][C:17]1[CH:16]=[C:15]([CH2:14][NH:13][C:12]2[C:8]([C:6]([NH:5][CH2:3][CH3:4])=[O:7])=[N:9][O:10][C:11]=2[C:24]2[CH:29]=[C:28]([Cl:30])[C:27]([OH:31])=[CH:26][C:25]=2[OH:32])[O:19][N:18]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 135895377HCID 135895377, compound

Product 1

HCID 136386265HCID 136386265, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Sodium borohydride (2 eq) was added portionwise at 0° C. to a solution of methyl 5-((3-(ethylcarbamoyl)-5-(5-chloro-2,4-dihydroxyphenyl) isoxazol-4-ylamino)methyl)isoxazole-3-carboxylate (0.34 mmol, 150 mg) in EtOH 95% (5 ml). After 30 min, few drops of a 5% HCl solution were added to the mixture and the solvent was evaporated under vacuo. The crude reaction mixture was diluted with H2O (10 ml) and extracted with AcOEt (2×10 ml). The combined organic phases were washed with brine, dried and filtered. Solvent was removed under vacuo and the crude product was purified by flash chromatography on silica gel (AcOEt/light petroleum).

Workup

  1. customthe solvent was evaporated under vacuo
  2. customThe crude reaction mixture
  3. extractionextracted with AcOEt (2×10 ml)
  4. washThe combined organic phases were washed with brine
  5. customdried
  6. filtrationfiltered
  7. customSolvent was removed under vacuo
  8. customthe crude product was purified by flash chromatography on silica gel (AcOEt/light petroleum)

Sources & evidence

ORD record
ord-3dfa858470e043c7a76f9cd6b6fc55e7
Source dataset
uspto-grants-2013_02
Patent number
US08383616B2

Reaction notes

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