HCID 19605201, compound → HCID 19605146, compound

HRID 1603481Notes

Reaction equation

HRID 1603481 reaction equation
B.[Na].[C:3]([O:7][C:8]([NH:10][CH2:11][C:12]1[S:13][C:14]([CH:17]=[O:18])=[CH:15][N:16]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4]>CO>[C:3]([O:7][C:8]([NH:10][CH2:11][C:12]1[S:13][C:14]([CH2:17][OH:18])=[CH:15][N:16]=1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

4

Reactant 2

HCID 19605201HCID 19605201, compoundHCID 178418435HCID 178418435, compound

Product 1

HCID 19605146HCID 19605146, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 330 mg potion of sodium boron hydride was added to 25 ml of a methanol solution containing 4.12 g of 2-(N-t-butoxycarbonylamino)methyl-5-formylthiazole under ice-cooling, and the mixture was then stirred at room temperature for 1 hour. Under reduced pressure, the solvent was distilled off, and water was added to the resulting residue, followed by extraction with ethyl acetate (80 ml×3). The organic layer was dried over anhydrous sodium sulfate and then filtered, and the solvent was evaporated under reduced pressure to obtain 2.17 g of 2-(N-t-butoxycarbonylamino)methyl-5-hydroxymethylthiazole.

Workup

  1. temperaturecooling
  2. distillationUnder reduced pressure, the solvent was distilled off
  3. additionwater was added to the resulting residue
  4. extractionfollowed by extraction with ethyl acetate (80 ml×3)
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-18c7289787f5487fb187a503b55703b4
Source dataset
uspto-grants-1999_11
Patent number
US05990101

Reaction notes

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