Lithium borohydride → HCID 21914863, compound

HRID 1246499Notes

Reaction equation

HRID 1246499 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:8]([C:10](OCC)=[O:11])[N:9]=1)(=[O:3])[CH3:2].[BH4-].[Li+]>C1COCC1>[CH2:15]([C:7]1[S:6][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[N:9][C:8]=1[CH:10]=[O:11])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 21914986HCID 21914986, compound

Product 1

HCID 21914863HCID 21914863, compoundYield 29.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 2-(acetylamino)-5-benzyl-1,3-thiazole-4-carboxylate (1.0 g) was dissolved in THF(20 ml), and then lithium borohydride (124 mg) was added portionwise to the solution at 0° C. The reaction mixture was refluxed for 4.5 hours and quenched with MeOH. The mixture was concentrated in vacuo, and purified by flash column chromatography over silica gel with CHCl3/MeOH (20:1) as an eluent. The residual amorphous substance was dissolved in MeOH (1 ml) and CHCl3 (8 ml). Then manganase(IV) oxide (1.26 g) was added to the solution under N2 atmosphere. The reaction mixture was stirred at r.t. for 12 hours, and filtered through a celite pad. The filtrate was concentrated in vacuo. The residue was purified by flash column chromatography over silica gel with CHCl3/MeOH (20:1) as an eluent to give N-(5-benzyl-4-formyl-1,3-thiazol-2-yl)acetamide (251 mg) as a pale yellow solid.

Workup

  1. temperatureThe reaction mixture was refluxed for 4.5 hours
  2. customquenched with MeOH
  3. concentrationThe mixture was concentrated in vacuo
  4. custompurified by flash column chromatography over silica gel with CHCl3/MeOH (20:1) as an eluent
  5. dissolutionThe residual amorphous substance was dissolved in MeOH (1 ml)
  6. additionThen manganase(IV) oxide (1.26 g) was added to the solution under N2 atmosphere
  7. filtrationfiltered through a celite pad
  8. concentrationThe filtrate was concentrated in vacuo
  9. customThe residue was purified by flash column chromatography over silica gel with CHCl3/MeOH (20:1) as an eluent

Sources & evidence

ORD record
ord-e21b5a32bbb14daba0ffa88c068da313
Source dataset
uspto-grants-2006_10
Patent number
US07125901B2

Reaction notes

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