Lithium Hydroxide → 232280-96-5

HRID 1582908Notes

Reaction equation

HRID 1582908 reaction equation
[C:1]([NH:8][CH2:9][C:10]1[S:11][C:12]([CH3:19])=[C:13]([C:15]([O:17]C)=[O:16])[N:14]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Li+].[OH-]>C(O)C.O>[C:1]([NH:8][CH2:9][C:10]1[S:11][C:12]([CH3:19])=[C:13]([C:15]([OH:17])=[O:16])[N:14]=1)([O:3][C:4]([CH3:5])([CH3:7])[CH3:6])=[O:2]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 21866496HCID 21866496, compound

Product 1

HCID 21866470232280-96-5

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Methyl 2-(N-Boc-aminomethyl)-5-methylthiazole-4-carboxylate (22.0 g, 77 mmol) was dissolved in ethanol (100 ml), and a solution of LiOH (2.2 g, 92 mmol) in water (50 ml) was added. After the mixture had been stirred for 30 minutes at room temperature, the ethanol was removed on a rotary evaporator and the solution which remained was diluted with water (70 ml). The aqueous phase was washed with ethyl acetate (3×) and brought to pH 2 with 20% strength NaHSO4 solution, during which process a pale brown oil separated out. The aqueous phase was extracted with dichloromethane and the combined organic extracts were dried (MgSO4) and concentrated in vacuo. The pale brown residue was extracted by stirring in diisopropyl ether. The colorless precipitate which remained was filtered off with suction and washed with diisopropyl ether. Yield: 6.9 g (25.4 mmol, 33%, colorless solid).

Workup

  1. customthe ethanol was removed on a rotary evaporator
  2. additionthe solution which remained was diluted with water (70 ml)
  3. washThe aqueous phase was washed with ethyl acetate (3×)
  4. customseparated out
  5. extractionThe aqueous phase was extracted with dichloromethane
  6. dry with materialthe combined organic extracts were dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. extractionThe pale brown residue was extracted
  9. stirringby stirring in diisopropyl ether
  10. filtrationThe colorless precipitate which remained was filtered off with suction
  11. washwashed with diisopropyl ether

Sources & evidence

ORD record
ord-75090c0d75764fc88f6e16d09bacc2db
Source dataset
uspto-grants-2004_05
Patent number
US06740647B1

Reaction notes

Loading…