Potassium Sodium Tartrate → HCID 90203282, compound

HRID 927038Notes

Reaction equation

HRID 927038 reaction equation
[C:1]([O:5][C:6](=[O:21])[NH:7][C:8]1[C:9]([C:13]2[CH:18]=[CH:17][C:16]([C:19]#N)=[CH:15][CH:14]=2)=[N:10][O:11][CH:12]=1)([CH3:4])([CH3:3])[CH3:2].CC(C[AlH]CC(C)C)C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=[O:34].[Na+].[K+]>C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:21])[NH:7][C:8]1[C:9]([C:13]2[CH:18]=[CH:17][C:16]([CH:19]=[O:34])=[CH:15][CH:14]=2)=[N:10][O:11][CH:12]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 9357Potassium Sodium TartrateHCID 14487Diisobutylaluminum hydride2×HCID 90203276HCID 90203276, compound

Product 1

HCID 90203282HCID 90203282, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of [3-(4-cyano-phenyl)-isoxazol-4-yl]-carbamic acid tert-butyl ester (1.88, 6.6 mmol) in toluene (50 mL) was cooled to 0° C. under Ar. DIBAL (6.7 mL, 1M in CH2Cl2, 6.7 mmol) was added dropwise to the solution and the reaction mixture was allowed to warm to rt and stirred for 1 h. DIBAL (6.7 mL, 1M in CH2Cl2, 6.7 mmol) was added again and the reaction mixture was stirred an additional 30 min. Saturated, aqueous Rochelle salt was added and the reaction mixture was stirred overnight. The phases were extracted three times with ethyl acetate. The combined organic phases were washed with brine and dried over MgSO4. Filtration followed by removal of volatiles under reduced pressure afforded a waxy solid from which [3-(4-Formyl-phenyl)-isoxazol-4-yl]-carbamic acid tert-butyl ester was isolated as a white solid (1.34 g, 70%) by column chromatography (50% ethyl acetate in hexane).

Workup

  1. stirringthe reaction mixture was stirred an additional 30 min
  2. stirringthe reaction mixture was stirred overnight
  3. extractionThe phases were extracted three times with ethyl acetate
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationFiltration
  7. customfollowed by removal of volatiles under reduced pressure

Sources & evidence

ORD record
ord-493045c6b5374ddd9af6fa1ab2b521f7
Source dataset
uspto-grants-2016_03
Patent number
US09290465B2

Reaction notes

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