2,6-Lutidine → HCID 58017529, compound

HRID 1642765Notes

Reaction equation

HRID 1642765 reaction equation
[Br:1][CH2:2][CH2:3][C@@H:4](O)[C:5]([O:7][CH2:8][CH3:9])=[O:6].O(S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O.N1C(C)=CC=CC=1C.[C:34]([O:38][C:39](=[O:42])[NH:40][NH2:41])([CH3:37])([CH3:36])[CH3:35]>C(Cl)Cl>[Br:1][CH2:2][CH2:3][C@H:4]([NH:41][NH:40][C:39]([O:38][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:42])[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

6

Reactant 4

HCID 79372,6-LutidineHCID 67749Trifluoromethanesulfonic anhydrideHCID 70091tert-Butyl carbazateHCID 54160780HCID 54160780, compound

Product 1

HCID 58017529HCID 58017529, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of ethyl (2R)-4-bromo-2-hydroxybutanoate (1.1 g, 5.2 mmol, prepared as described in J. Med. Chem. 2003, 46, 2057 or J. Am. Chem. Soc., 2004, 126, 12432 and Tetrahedron Letters 1997, 38, 4935-4938, in dry DCM (20 mL) at 0° C. was added Tf2O (1.62 g, 5.7 mmol) via syringe. After 5 min, 2,6-lutidine (0.67 g, 6.2 mmol) was added. After another 5 min, t-butylcarbazate (1.38 g, 10.4 mmol) in DCM (5 mL) was added. The solution was allowed to attain rt and stirred overnight. The solvent was evaporated and the residue was purified using flash chromatography (heptane/EtOAc 4:1, 3:1, 2:1) to give the slightly impure tert-butyl 2-[(1S)-3-bromo-1-(ethoxycarbonyl)propyl]hydrazinecarboxylate (1.65 g, 97%) as an oil.

Workup

  1. waitAfter another 5 min
  2. customto attain rt
  3. customThe solvent was evaporated
  4. customthe residue was purified

Sources & evidence

ORD record
ord-08d5d36c4ecc403b84da2414e70831f9
Source dataset
uspto-grants-2012_02
Patent number
US08119673B2

Reaction notes

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