Sodium Carbonate → tert-butyl (2S)-2-aminohexanoate

HRID 2185593Notes

Reaction equation

HRID 2185593 reaction equation
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH2:4][CH2:5][CH3:6].C(O[C:14]([CH3:17])([CH3:16])[CH3:15])(=O)C.C([O-])([O-])=O.[Na+].[Na+]>>[CH3:15][C:14]([O:8][C:7](=[O:9])[C@H:2]([CH2:3][CH2:4][CH2:5][CH3:6])[NH2:1])([CH3:17])[CH3:16]

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 10908tert-Butyl acetateHCID 21236Caprine

Product 1

HCID 12451446tert-butyl (2S)-2-aminohexanoateYield 76.4%

Conditions

Temperature
20 °C

Procedure

To a suspension of L-norleucine (commercial product) (13.1 g; 0.1 mol) in t-butyl acetate (600 mL; 4.45 mol) maintained at 20° C., 70% aq. HClO4 (10.3 mL; 0.12 mol) was added in 10 min. The reaction was maintained at r.t. for 7 h. Saturated aq. Na2CO3 was slowly added until pH 9 was reached and the organic phase was separated and concentrated. The oily residue was dissolved in Et2O (250 mL) and extracted with 1N HCl (120 mL). The aqueous phase was basified to pH 10 with 1 N NaOH and extracted with Et2O (400 mL). The organic layer, dried over Na2SO4, was concentrated to give the desired compound (14.3 g; 76.4 mmol). Yield 76%.

Workup

  1. temperatureThe reaction was maintained at r.t. for 7 h
  2. customthe organic phase was separated
  3. concentrationconcentrated
  4. dissolutionThe oily residue was dissolved in Et2O (250 mL)
  5. extractionextracted with 1N HCl (120 mL)
  6. extractionextracted with Et2O (400 mL)
  7. dry with materialThe organic layer, dried over Na2SO4
  8. concentrationwas concentrated

Sources & evidence

ORD record
ord-15373cf836a044a3b7c27bb093f5fae9
Source dataset
uspto-grants-2002_06
Patent number
US06403055B1

Reaction notes

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