Hydrogen Bromide → HCID 13615094, compound

HRID 2228859Notes

Reaction equation

HRID 2228859 reaction equation
N[C@H:2]([C:7]([OH:9])=[O:8])[C@H:3]([CH2:5][CH3:6])[CH3:4].N([O-])=O.[Na+].[BrH:14]>>[Br:14][C@@H:2]([C@@H:3]([CH3:4])[CH2:5][CH3:6])[C:7]([OH:9])=[O:8]

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 6306L-IsoleucineHCID 23668193Sodium Nitrite

Product 1

HCID 13615094HCID 13615094, compoundYield 55%

Procedure

To a cooled (0° C.) solution of L-Isoleucine (66 g) dissolved in HBr (6N, 500 ml) was added dropwise a solution of sodium nitrite (35 g in 100 ml water). The reaction was stirred overnight at room temperature and then extracted with EtOAc (3×150 ml). The combined organic extracts washed with 10% sodium bisulfit solution, water, saturated brine, dried over MgSO4, filtered and concentrated. The product a yellowish oil (53.9 g) was obtained in 55% yield. (The product can be purified by distillation and crystallization from PE). (see FIG. 6)

Workup

  1. extractionextracted with EtOAc (3×150 ml)
  2. washThe combined organic extracts washed with 10% sodium bisulfit solution, water, saturated brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-668ef537a7764872b4963944f5816078
Source dataset
uspto-grants-2002_07
Patent number
US06417399B1

Reaction notes

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