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

HRID 2120950Notes

Reaction equation

HRID 2120950 reaction equation
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[OH-].[Na+].[O:12](C(OC(C)(C)C)=O)[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=O.Cl>C1COCC1>[C:13]([NH:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5])([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6106L-LeucineHCID 14798Sodium HydroxideHCID 90495Di-tert-butyl dicarbonate

Product 1

HCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-Yield 115.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

19.7 g (0.15 mole) L-Leucine 4 was suspended in 200 mlH2O and 6.75 g (0.17 mole) NaOH was added. The clear solution was cooled to <10° C. and a solution of 36 g (0.165 mole) (BOC)2O in 100 ml THF was added dropwise keeping T<10° C. (30 minutes). After stirring for 4 hours at room temperature the mixture was acidified to pH2 by adding 1N HCl. The mixture was extracted with EtOAc (250, 100 and 100 ml), the combined organic layers were dried on Na2SO4 and evaporated, yielding 40 g (>100%) 5 as a colorless oil which contained some THF but was used as such.

Workup

  1. additionwas added
  2. temperatureThe clear solution was cooled to <10° C.
  3. extractionThe mixture was extracted with EtOAc (250, 100 and 100 ml)
  4. customthe combined organic layers were dried on Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-cc4244cffcc14bfe81aafb3ef4ae8754
Source dataset
uspto-grants-2004_02
Patent number
US06693167B1

Reaction notes

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