Glycine → Fmoc-Gly-OH

HRID 499747Notes

Reaction equation

HRID 499747 reaction equation
[NH2:1][CH2:2][C:3]([OH:5])=[O:4].[CH:6]1[C:18]2[CH:17]([CH2:19][O:20][C:21](Cl)=[O:22])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]=2[CH:9]=[CH:8][CH:7]=1.O>O1CCOCC1>[NH:1]([C:21]([O:20][CH2:19][CH:17]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]2[C:18]1=[CH:6][CH:7]=[CH:8][CH:9]=2)=[O:22])[CH2:2][C:3]([OH:5])=[O:4]

Participants

5

Reactant 3

HCID 750GlycineHCID 962WaterHCID 343679-Fluorenylmethyl chloroformate

Product 1

HCID 93124Fmoc-Gly-OH

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Glycine (Gly) (0.5 g, 6.66 mmole) was dissolved in 10% NaCO3 (14 ml) under stirring in a 50-ml flask. To the resulting solution, which had been put into an ice bath, 9-fluorenylmethoxycarbonyl chloride (Fmoc-Cl) (1.72 g, 6.66 mmol) in dioxane (12 ml) was gradually added. The reaction mixture was stirred at room temperature for 4 hours, and water (150 ml) was then added. The aqueous phase layer was separated from the reaction mixture and stripped with ether three times (75 ml×3). The stripped aqueous layer was acidified with 2N HCl aqueous solution to a pH value of 2, followed by extraction with ethyl acetate three times (75 ml×3). The organic phase layer was recovered and concentrated to obtain crude product of 1.70 g. The crude product was recrystallized in a mixed solvent of ethyl acetate hexane=1:2 (30 ml), and white solid denoted as Fmoc-Gly was obtained after filtration at a reduced pressure. Yield: 1.69 g (85%).

Workup

  1. customTo the resulting solution, which had been put into an ice bath
  2. stirringThe reaction mixture was stirred at room temperature for 4 hours
  3. customThe aqueous phase layer was separated from the reaction mixture
  4. extractionfollowed by extraction with ethyl acetate three times (75 ml×3)
  5. customThe organic phase layer was recovered
  6. concentrationconcentrated
  7. customto obtain crude product of 1.70 g
  8. customThe crude product was recrystallized in a mixed solvent of ethyl acetate hexane=1:2 (30 ml), and white solid
  9. customwas obtained
  10. filtrationafter filtration at a reduced pressure

Sources & evidence

ORD record
ord-0788c6045c9a4c83b137b87cdb91d962
Source dataset
uspto-grants-2010_08
Patent number
US07767707B2

Reaction notes

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