Lithium Hydroxide → Fmoc-L-2-Furylalanine

HRID 1779974Notes

Reaction equation

HRID 1779974 reaction equation
[NH2:1][C@@H:2]([CH2:7][C:8]1[O:9][CH:10]=[CH:11][CH:12]=1)[C:3]([O:5]C)=[O:4].[Li+].[OH-].C(Cl)(Cl)Cl.CO.N.C([O-])(O)=O.[Na+].[CH:27]1[C:39]2[CH:38]([CH2:40][O:41][C:42](Cl)=[O:43])[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:31]=2[CH:30]=[CH:29][CH:28]=1>O1CCOCC1>[CH:27]1[C:39]2[CH:38]([CH2:40][O:41][C:42]([NH:1][C@@H:2]([CH2:7][C:8]3[O:9][CH:10]=[CH:11][CH:12]=3)[C:3]([OH:5])=[O:4])=[O:43])[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:31]=2[CH:30]=[CH:29][CH:28]=1

Participants

7

Reactant 5

HCID 3939Lithium HydroxideHCID 343679-Fluorenylmethyl chloroformateHCID 516892Sodium BicarbonateHCID 14519820HCID 14519820, compoundHCID 21866414Chloroform methanol ammonia

Product 1

HCID 2734451Fmoc-L-2-Furylalanine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

Methyl (S)-2-amino-3-(2-furyl)propionate (1 g, 6.5 mmol) was mixed with 2M LiOH (3.27 ml, 6.5 mmol) and dioxane (3.27 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 (9.75 ml, 9.75 mmol) and 9-fluorenylmethyloxycarbonyl chloride (2.5 g, 9.75 mmol) dissolved in dioxane (10 ml) were added to the above solution and the stirring continued for a further 1 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 1 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-fe7d2faf56fc496689e6bb1e9635f2c7
Source dataset
uspto-grants-1997_05
Patent number
US05629293

Reaction notes

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