Hexanoyl bromide → 2-Amino-3-methylpentanoic hexanoic anhydride

HRID 1788301Notes

Reaction equation

HRID 1788301 reaction equation
[C:1](Br)(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[NH2:9][CH:10]([CH:14]([CH3:17])[CH2:15][CH3:16])[C:11]([O-:13])=[O:12].[Na+]>>[C:1]([O:12][C:11](=[O:13])[CH:10]([NH2:9])[CH:14]([CH3:17])[CH2:15][CH3:16])(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

3

Reactant 2

HCID 13226800Hexanoyl bromide2×HCID 23662724Sodium 2-amino-3-methylpentanoate

Product 1

HCID 250061692-Amino-3-methylpentanoic hexanoic anhydride

Procedure

Finally, in a dry 2-necked, round bottomed flask, fixed with a separatory funnel, containing 10.81 g (60 mmol) of the prepared hexanoyl bromide, and side arm water condenser fixed with a dry receiving flask, is placed 11.03 g (72 mmol) of sodium 2-amino-3-methylpentanoate. The round bottomed flask is placed in an ice bath and the hexanoyl bromide is added drop wise. After addition is completed the mixture is shaken and the ice bath is replaced by a heating mantle. The flask is then heated until no more solution is dropping into the receiving flask. This crude distillate is then further fractionally distilled to yield 2-amino-3-methylpentanoic hexanoic anhydride.

Workup

  1. customFinally, in a dry 2-necked, round bottomed flask, fixed with a separatory funnel
  2. customThe round bottomed flask is placed in an ice bath
  3. additionAfter addition
  4. temperatureThe flask is then heated until no more solution
  5. distillationThis crude distillate is then further fractionally distilled

Sources & evidence

ORD record
ord-06008332fead487594dfab2b7e8eb607
Source dataset
uspto-grants-2009_03
Patent number
US07511162B2

Reaction notes

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