Ammonia → L-Norleucine, 6-azido-, methyl ester

HRID 1779967Notes

Reaction equation

HRID 1779967 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][CH2:7][C@H:8]1[C:13]([O:14][CH3:15])=N[C@H](C(C)C)C(OC)=[N:9]1)=[N+:2]=[N-:3].Cl.[OH2:22].N>O1CCOCC1>[NH2:9][C@@H:8]([CH2:7][CH2:6][CH2:5][CH2:4][N:1]=[N+:2]=[N-:3])[C:13]([O:14][CH3:15])=[O:22]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 962WaterHCID 86750806HCID 86750806, compound

Product 1

HCID 54574963L-Norleucine, 6-azido-, methyl ester

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1-Azido-4-[(2R,5S)-3,6-dimethoxy-2-isopropyl-2,5-dihydro-5-pyrazinyl]butane (2.17 g, 7.72 mmol) was dissolved in 30 ml dioxane and a solution of 1.28 ml conc. HCl in 30 ml water (15.45 mmol) was added dropwise, the mixture stirred under argon at ambient temperature overnight. Ammonia solution was added until pH 9 was reached, the solution extracted with chloroform, dried (MgSO4), and the valine methyl ester was removed by bulb-to-bulb distillation (0.05 torr, 25° C.).

Workup

  1. extractionthe solution extracted with chloroform
  2. dry with materialdried (MgSO4)
  3. customthe valine methyl ester was removed by bulb-to-bulb distillation (0.05 torr, 25° C.)

Sources & evidence

ORD record
ord-be04d37688bb407089dd907a6668fc0e
Source dataset
uspto-grants-1997_05
Patent number
US05629293

Reaction notes

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