Hydrochloric Acid → L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-

HRID 2120951Notes

Reaction equation

HRID 2120951 reaction equation
[NH2:1][CH2:2][C:3]([OH:5])=[O:4].[OH-].[Na+].[O:8](C(OC(C)(C)C)=O)[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=O.Cl>O.C1COCC1>[C:9]([NH:1][C@H:2]([C:3]([OH:5])=[O:4])[CH2:13][CH:12]([CH3:15])[CH3:14])([O:11][C:12]([CH3:14])([CH3:13])[CH3:15])=[O:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 750GlycineHCID 14798Sodium HydroxideHCID 90495Di-tert-butyl dicarbonate

Product 1

HCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-Yield 248.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

18.8 g (0.25 mole) Glycine 18 was suspended in 250 ml H2O and 11 g (0.275 mole) NaOH was added. The clear solution was cooled to <10° C. and a solution of 60 g (0.165 mole) (BOC)2O in 250 ml THF was added dropwise keeping T<10° C. (20 minutes). After stirring for 20 hours at room temperature the mixture was acidified to pH1 by adding 1N HCl. The mixture was extracted with EtOAc (250, 100 and 100 ml), the combined organic layers were dried on MgSO4 and evaporated, yielding 47.5 g (>100%) 5 as a colourless oil which contained some THF but was used as such.

Workup

  1. temperatureThe clear solution was cooled to <10° C.
  2. extractionThe mixture was extracted with EtOAc (250, 100 and 100 ml)
  3. customthe combined organic layers were dried on MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-bb26164aec504ebcb312573c40eb7f40
Source dataset
uspto-grants-2004_02
Patent number
US06693167B1

Reaction notes

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