Hydrogen Bromide → HCID 7018865, compound

HRID 482580Notes

Reaction equation

HRID 482580 reaction equation
Br.[CH2:2]([O:5][C:6](=[O:19])[C@H:7]([CH:16]([CH3:18])[CH3:17])[NH:8]C(OC(C)(C)C)=O)[CH:3]=[CH2:4]>C(Cl)(Cl)Cl>[CH2:2]([O:5][C:6](=[O:19])[C@H:7]([CH:16]([CH3:17])[CH3:18])[NH2:8])[CH:3]=[CH2:4]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 53841977HCID 53841977, compound

Product 1

HCID 7018865HCID 7018865, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
-20 °C

Procedure

A solution of 100 mL CHCl3 /10% MeOH saturated at -20° C. with HBr gas was cooled to -78° C. To this solution was added N-(tert-Butyloxycarbonyl)-L-valine allyl ester (5.10 g, 19.8 mmol) dissolved in 10 mL CHCl3. The mixture was warmed to -20° C., stirred 15 min then poured into ice cold saturated NaHCO3 (300 mL). The organic phase was separated. The aqueous phase was washed with 50 mL of CHCl3. The organic phases were combined, dried over Na2 SO4, concentrated to afford 3.10 g (99%) of the title compound which was used without further purification.

Workup

  1. customThe organic phase was separated
  2. washThe aqueous phase was washed with 50 mL of CHCl3
  3. customdried over Na2 SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ae6431784f874d0692c1205e7dbaa64b
Source dataset
uspto-grants-1998_08
Patent number
US05798442

Reaction notes

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