Hydrogen Bromide → HCID 2734540, compound

HRID 1604221Notes

Reaction equation

HRID 1604221 reaction equation
Cl.N[C@@H:3]([C:8]([OH:10])=[O:9])[CH2:4][CH2:5][CH2:6][NH2:7].[OH-].[K+].C(N1[C:22](=[O:23])[C:21]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]2[C:19]1=[O:28])(OCC)=O.[BrH:29].[Br-].[K+].N([O-])=O.[Na+]>O.S([O-])([O-])(=O)=O.[Cu+2]>[Br:29][C@H:3]([CH2:4][CH2:5][CH2:6][N:7]1[C:22](=[O:23])[C:21]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]2[C:19]1=[O:28])[C:8]([OH:10])=[O:9]

Participants

9

Reactant 6

HCID 260Hydrogen Bromide2×HCID 14797Potassium Hydroxide2×HCID 31187N-CarbethoxyphthalimideHCID 253877Potassium BromideHCID 443122D-Ornithine monohydrochlorideHCID 23668193Sodium Nitrite

Product 1

HCID 2734540HCID 2734540, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 962WaterSolvent2×

Procedure

A solution of D-ornithine hydrochloride (35 g, 0.208 mol) in water (350 ml) was treated with copper (II) sulphate (16.6 g, 0.104 mol). 5M Potassium hydroxide (ca. 40 ml) was added to pH 3 then N-carboethoxyphthalimide (45.5 g, 0.208 mol) was added and the pH maintained at 9-10 by the addition of 5M potassium hydroxide (ca. 55 ml). After 2 h, 48% hydrobromic acid was added to pH 0.4 (ca. 77 ml) and any resulting precipitate removed by filtration. The filtrate was cooled to <5° C., then treated with further hydrobromic acid (152 ml) and potassium bromide (59 g, 0.5 mol). The mixture was then treated dropwise over 45 min with a solution of sodium nitrite (28.6 g, 0.41 mol) in water (275 ml) whilst maintaining a temperature of <5° C. The mixture was then stirred at <5° C. overnight. The resulting precipitate was then removed by filtration, dissolved in ethyl acetate (400 ml) and the solution washed with water (2×200 ml) and brine (200 ml), dried (MgSO4) and evaporated in vacuo to provide the title compound (40.6 g, 47%) as a cream solid.

Workup

  1. customany resulting precipitate removed by filtration
  2. temperatureThe filtrate was cooled to <5° C.
  3. temperaturewhilst maintaining a temperature of <5° C
  4. customThe resulting precipitate was then removed by filtration
  5. dissolutiondissolved in ethyl acetate (400 ml)
  6. washthe solution washed with water (2×200 ml) and brine (200 ml)
  7. dry with materialdried (MgSO4)
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-f3748d5fc31c4f178dc994cac6911155
Source dataset
uspto-grants-1999_11
Patent number
US05994312

Reaction notes

Loading…