Ethanol → HCID 22170722, compound

HRID 1822874Notes

Reaction equation

HRID 1822874 reaction equation
[Li+].[BH4-].[Br:3][C:4]1[S:8][C:7]([NH:9][C:10](=[O:17])[CH2:11][C:12](OCC)=[O:13])=[N:6][CH:5]=1.C(O)C>CCOCC>[Br:3][C:4]1[S:8][C:7]([NH:9][C:10](=[O:17])[CH2:11][CH2:12][OH:13])=[N:6][CH:5]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 4148881Lithium borohydrideHCID 22170496HCID 22170496, compound

Product 1

HCID 22170722HCID 22170722, compoundYield 58.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of LiBH4 (44 mg, 2.02 mmol), ethyl 3-[(5-bromo-1,3-thiazol-2-yl)amino]-3-oxopropanoate (340 mg, 1.16 mmol), ethanol (0.082 ml, 2.02 mmol), and Et2O (50 ml) was refluxed for 20 min. The reaction was quenched with 1 N hydrochloric acid with ice-cooling. The mixture was then diluted with water and extracted with dichloromethane. The extract was dried and the solvent was evaporated under reduced pressure. Purification by silica gel chromatography (dichloromethane/methanol=98:2 and then 95:5) yielded the title compound as a white solid (0.17 g; 52%).

Workup

  1. temperaturewas refluxed for 20 min
  2. customThe reaction was quenched with 1 N hydrochloric acid with ice-
  3. temperaturecooling
  4. additionThe mixture was then diluted with water
  5. extractionextracted with dichloromethane
  6. customThe extract was dried
  7. customthe solvent was evaporated under reduced pressure
  8. customPurification by silica gel chromatography (dichloromethane/methanol=98:2

Sources & evidence

ORD record
ord-90843c144b0b4dee9c73cf6823f18fbc
Source dataset
uspto-grants-2006_05
Patent number
US07037929B1

Reaction notes

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