Methanol → 2-(N-t-butoxycarbonylamino)methyl-4-methoxycarbonylaminothiazole

HRID 1603467Notes

Reaction equation

HRID 1603467 reaction equation
CN([CH:4]=[O:5])C.[C:6]([O:10][C:11]([NH:13][CH2:14][C:15]1[S:16][CH:17]=[C:18](C(O)=O)[N:19]=1)=[O:12])([CH3:9])([CH3:8])[CH3:7].C([N:25]([CH2:28]C)CC)C.C[OH:31]>>[C:6]([O:10][C:11]([NH:13][CH2:14][C:15]1[S:16][CH:17]=[C:18]([NH:25][C:28]([O:5][CH3:4])=[O:31])[N:19]=1)=[O:12])([CH3:7])([CH3:8])[CH3:9]

Participants

5

Reactant 4

HCID 887MethanolHCID 6228DimethylformamideHCID 8471TriethylamineHCID 101990462-(((Tert-butoxycarbonyl)amino)methyl)thiazole-4-carboxylic acid

Product 1

HCID 196051602-(N-t-butoxycarbonylamino)methyl-4-methoxycarbonylaminothiazole

Conditions

Temperature
100 °C

Procedure

To 50 ml of a dry DMF solution containing 2.583 g of 2-(N-t-butoxycarbonylamino)methylthiazol-4-carboxylic acid, 1.53 ml of triethylamine and 2.37 ml of azido diphenylphosphate were added. Immediately after the mixed solution was then heated at an oil temperature of 100° C. for 10 minutes under stirring, it was cooled on ice to return its temperature to room temperature. Further, 2.0 ml of dry methanol was added, and after heating at an oil temperature of 80° C. for 30 minutes, the solvent was evaporated under reduced pressure. The residue was diluted with 100 ml of ethyl acetate and then washed with a 15% aqueous potassium carbonate solution, and the separated organic layer was then combined with a liquid extracted from the aqueous layer with 50 ml of ethyl acetate. Furthermore, the solution was washed with distilled water and a saturated saline solution in succession, and then dried over anhydrous magnesium sulfate. Afterward, the solvent was evaporated under reduced pressure to obtain an oil, and this oil was then purified by a silica gel column chromatograph to obtain 817 mg of 2-(N-t-butoxycarbonylamino)methyl-4-methoxycarbonylaminothiazole as a slightly red crystal.

Workup

  1. additionwere added
  2. temperatureit was cooled on ice
  3. customto room temperature
  4. temperatureafter heating at an oil temperature of 80° C. for 30 minutes
  5. customthe solvent was evaporated under reduced pressure
  6. additionThe residue was diluted with 100 ml of ethyl acetate
  7. washwashed with a 15% aqueous potassium carbonate solution
  8. extractionextracted from the aqueous layer with 50 ml of ethyl acetate
  9. washFurthermore, the solution was washed with distilled water
  10. dry with materiala saturated saline solution in succession, and then dried over anhydrous magnesium sulfate
  11. customAfterward, the solvent was evaporated under reduced pressure
  12. customto obtain an oil
  13. customthis oil was then purified by a silica gel column chromatograph

Sources & evidence

ORD record
ord-c9ea31408ae14686aee8d2b02457334c
Source dataset
uspto-grants-1999_11
Patent number
US05990101

Reaction notes

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