Acetone → 165667-51-6

HRID 1376612Notes

Reaction equation

HRID 1376612 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]1[N:14](C(OCC)=O)[CH:13]=[CH:12][S:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Li+].C[C:23](C)=[O:24]>C(O)C>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[S:11][CH:12]=[C:13]([CH2:23][OH:24])[N:14]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 180AcetoneHCID 4148881Lithium borohydrideHCID 22916674HCID 22916674, compound

Product 1

HCID 22916663165667-51-6Yield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 0.52 g of ethyl 2-(tert-butoxycarbonylamino)methylthiazole-3-carboxylate in 10 ml of ethanol was added 200 mg of lithium borohydride, and the mixture was stirred at room temperature for 30 minutes. To this reaction solution was added 2 ml of acetone. The mixture was stirred for an additional 30 minutes, and then concentrated under reduced pressure. To the residue were added 15 ml of dichloromethane and 15 ml of a saturated saline solution, and the mixture was stirred for 10 minutes. The organic layer was separated, and the aqueous layer was extracted with dichloromethane (5 ml×2). The combined organic layers were dried over anhydrous magnesium sulfate, and concentrated to dryness under reduced pressure to give 0.357 g (yield 81%) of the title compound.

Workup

  1. stirringThe mixture was stirred for an additional 30 minutes
  2. concentrationconcentrated under reduced pressure
  3. additionTo the residue were added 15 ml of dichloromethane and 15 ml of a saturated saline solution
  4. stirringthe mixture was stirred for 10 minutes
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with dichloromethane (5 ml×2)
  7. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  8. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-62d17cbfcfab44438dbb68994d2441a5
Source dataset
uspto-grants-1997_09
Patent number
US05663162

Reaction notes

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