Lithium Hydroxide → HCID 53773405, compound

HRID 1779977Notes

Reaction equation

HRID 1779977 reaction equation
[NH2:1][C@@H:2]([CH2:7][C:8]1[C:9]([CH3:14])=[N:10][O:11][C:12]=1[CH3:13])[C:3]([O:5]C)=[O:4].[Li+].[OH-].C(Cl)(Cl)Cl.CO.N.C([O-])(O)=O.[Na+].[CH:29]1[C:41]2[CH:40]([CH2:42][O:43][C:44](Cl)=[O:45])[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[C:33]=2[CH:32]=[CH:31][CH:30]=1>O1CCOCC1>[CH:29]1[C:41]2[CH:40]([CH2:42][O:43][C:44]([NH:1][C@@H:2]([CH2:7][C:8]3[C:9]([CH3:14])=[N:10][O:11][C:12]=3[CH3:13])[C:3]([OH:5])=[O:4])=[O:45])[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[C:33]=2[CH:32]=[CH:31][CH:30]=1

Participants

7

Reactant 5

HCID 3939Lithium HydroxideHCID 343679-Fluorenylmethyl chloroformateHCID 516892Sodium BicarbonateHCID 21866414Chloroform methanol ammoniaHCID 28323176HCID 28323176, compound

Product 1

HCID 53773405HCID 53773405, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

Methyl (S)-2-amino-3-(3,5-dimethyl-4-isoxazolyl)propionate (1.3 g, 6.6 mmol) was mixed with 2M LiOH (3.3 ml, 6.6 mmol) and dioxane (3.3 ml) at 0° C. and stirred overnight under N2. The next day a TLC control (CHCl3 /MeOH/NH3 aq 1/1/0.1) of the reaction mixture showed no ester present. 1M NaHCO3 (10 ml, 10 mmol) and 9-fluorenylmethyloxycarbonyl chloride (2.6 g, 10 mmol) dissolved in dioxane (10 ml) were added to the above solution and the stirring continued for a further hour. Dioxane was removed under reduced pressure and the aqueous solution acidified with a 10% KHSO4 solution to pH 2. The solution was extracted with CHCl3 (3×20 ml), dried (MgSO4) evaporated and purified by flash chromatography (Hexane/ethyl acetate/acetic acid 10/10/1).

Workup

  1. additionwere added to the above solution
  2. waitthe stirring continued for a further hour
  3. customDioxane was removed under reduced pressure
  4. extractionThe solution was extracted with CHCl3 (3×20 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. custompurified by flash chromatography (Hexane/ethyl acetate/acetic acid 10/10/1)

Sources & evidence

ORD record
ord-29aadcd6a6b840388aa787eea7729eb5
Source dataset
uspto-grants-1997_05
Patent number
US05629293

Reaction notes

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