Water → HCID 86654274, compound

HRID 2200317Notes

Reaction equation

HRID 2200317 reaction equation
[Br:1][C:2]1[C:3]([NH:9][CH2:10][C:11]([O:13]CC)=[O:12])=[N:4][CH:5]=[C:6]([Br:8])[N:7]=1.[OH-].[Na+].O.P(=O)(O)(O)O>CCCCCCC.O1CCCC1>[Br:1][C:2]1[C:3]([NH:9][CH2:10][C:11]([OH:13])=[O:12])=[N:4][CH:5]=[C:6]([Br:8])[N:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 1004Phosphoric AcidHCID 14798Sodium HydroxideHCID 57550751Ethyl 2-(3,5-dibromopyrazin-2-ylamino)acetate

Product 1

HCID 86654274HCID 86654274, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8900HeptaneSolvent

Procedure

Ethyl 2-(3,5-dibromopyrazin-2-ylamino)acetate (1 equiv), tetrahydrofuran and sodium hydroxide in water (1.1 equiv) were combined and stirred at room temperature overnight. The reaction mixture was treated with dilute phosphoric acid (1.9 equiv) and heptane. The organic layer was concentrated to about 75% of its original volume and further distilled with addition of heptane until the reaction mixture was 80° C. The solution was treated with seed and distillation with addition of heptane was continued until reaching 85° C. The slurry was cooled and filtered, and the solids washed with heptane and dried to obtain 2-((3,5-dibromopyrazin-2-yl)amino)acetic acid as a solid. MS (ESI) m/z 309.9 [M+1].

Workup

  1. concentrationThe organic layer was concentrated to about 75% of its original volume
  2. distillationfurther distilled with addition of heptane until the reaction mixture
  3. customwas 80° C
  4. additionThe solution was treated with seed and distillation with addition of heptane
  5. customuntil reaching 85° C
  6. temperatureThe slurry was cooled
  7. filtrationfiltered
  8. washthe solids washed with heptane
  9. customdried

Sources & evidence

ORD record
ord-9c452922cfe749dc95d0d424ba86356f
Source dataset
uspto-grants-2016_06
Patent number
US09359364B2

Reaction notes

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