Hydrochloric Acid → HCID 69051372, compound

HRID 1452507Notes

Reaction equation

HRID 1452507 reaction equation
Cl.[NH2:2][CH:3]([CH2:7][NH2:8])[C:4]([OH:6])=[O:5].[Br:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([C:18]([C:20]2[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][CH:21]=2)=O)=O)=[CH:12][CH:11]=1>>[Br:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[N:8]=[CH:7][C:3]([C:4]([OH:6])=[O:5])=[N:2][C:18]=2[C:20]2[CH:21]=[CH:22][C:23]([Br:26])=[CH:24][CH:25]=2)=[CH:14][CH:15]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 3642,3-Diaminopropionic acidHCID 964304,4'-Dibromobenzil

Product 1

HCID 69051372HCID 69051372, compound

Procedure

The title compound was prepared essentially as described in Preparation A step (a), using monohydrochloride of 2,3-diaminopropionic acid (600 mg, 4.26 mmol) and 4,4′-dibromobenzil (1.745 g, 4.26 mmol, 90%) as starting materials. The reaction mixture was refluxed for 2 hours and air was bubbled through for 1 hour. Hydrochloric acid (aq, 2 M) was added until pH 2. The mixture was evaporated under reduced pressure and the residue was dissolved in water. The solution was extracted with diethyl ether, the combined diethyl ether phases were dried (MgSO4), filtered and evaporated under reduced pressure. The crude product (500 mg, 27%) was used in steps described below without further purification. MS m/z 435, 437, 439 (M+H)+.

Workup

  1. customas described in Preparation A step (a)
  2. temperatureThe reaction mixture was refluxed for 2 hours
  3. customair was bubbled through for 1 hour
  4. additionHydrochloric acid (aq, 2 M) was added until pH 2
  5. customThe mixture was evaporated under reduced pressure
  6. dissolutionthe residue was dissolved in water
  7. extractionThe solution was extracted with diethyl ether
  8. dry with materialthe combined diethyl ether phases were dried (MgSO4)
  9. filtrationfiltered
  10. customevaporated under reduced pressure
  11. customdescribed below without further purification

Sources & evidence

ORD record
ord-0f2ff7e20ac94fc283e8a72374666ec9
Source dataset
uspto-grants-2009_01
Patent number
US07473693B2

Reaction notes

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