Hydrochloric Acid → HCID 59570885, compound

HRID 2192933Notes

Reaction equation

HRID 2192933 reaction equation
[CH2:1]([O:4][C:5]([NH:7][C:8]1[S:9][CH:10]=[C:11]([C:13]([OH:20])([CH3:19])[C:14]([O:16][CH2:17][CH3:18])=O)[N:12]=1)=[O:6])[CH:2]=[CH2:3].[BH4-].[Na+].[OH2:23].Cl>O1CCOCC1>[C:17]([O:16][CH2:14][C:13]([C:11]1[N:12]=[C:8]([NH:7][C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[O:6])[S:9][CH:10]=1)([OH:20])[CH3:19])(=[O:23])[CH3:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 57956666HCID 57956666, compound

Product 1

HCID 59570885HCID 59570885, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of ethyl 2-(2-{[(allyloxy)carbonyl]amino}-1,3-thiazol-4-yl)-2-hydroxypropionate (2.75 g) in 1,4-dioxane (25 mL) was added sodium borohydride (0.962 g) under ice-cooling. Further, water (0.5 mL) was added thereto at room temperature, followed by stirring at room temperature for 2 hours. Concentrated hydrochloric acid (8 mL) was added thereto at an internal temperature of 20° C. or lower under ice-cooling, followed by concentration. A white solid was separated by filtration while washing the obtained residue with methanol. The obtained white solid was dissolved in pyridine (15 mL), and acetic anhydride (2.59 mL) was added thereto at room temperature, followed by stirring for 2.5 hours. To the reaction mixture was added water at room temperature, followed by extraction with ethyl acetate. The organic layer was sequentially washed with 1 M hydrochloric acid, saturated aqueous sodium bicarbonate, and saturated brine, and then dried over anhydrous magnesium sulfate. After concentration, 2-(2-{[(allyloxy)carbonyl]amino}-1,3-thiazol-4-yl)-2-hydroxypropyl acetate (2.71 g) was obtained as a pale yellow oily substance.

Workup

  1. temperaturecooling
  2. customat room temperature
  3. temperatureat an internal temperature of 20° C. or lower under ice-cooling
  4. concentrationfollowed by concentration
  5. customA white solid was separated by filtration
  6. washwhile washing the obtained residue with methanol
  7. dissolutionThe obtained white solid was dissolved in pyridine (15 mL)
  8. additionacetic anhydride (2.59 mL) was added
  9. customat room temperature
  10. stirringby stirring for 2.5 hours
  11. additionTo the reaction mixture was added water at room temperature
  12. extractionfollowed by extraction with ethyl acetate
  13. washThe organic layer was sequentially washed with 1 M hydrochloric acid, saturated aqueous sodium bicarbonate, and saturated brine
  14. dry with materialdried over anhydrous magnesium sulfate
  15. concentrationAfter concentration

Sources & evidence

ORD record
ord-ec32d6f57d6843579ef23271c40db05f
Source dataset
uspto-grants-2012_12
Patent number
US08329707B2

Reaction notes

Loading…