4-(Bromomethyl)benzoic acid → HCID 18316679, compound

HRID 276708Notes

Reaction equation

HRID 276708 reaction equation
[Br:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1.C1C=CC2N(O)N=NC=2C=1.[C:22]([C:24]([NH:27][C:28](=[O:35])[CH:29]([NH2:34])[CH2:30][CH:31]([CH3:33])[CH3:32])([CH3:26])[CH3:25])#[N:23]>CN(C)C=O>[C:22]([C:24]([NH:27][C:28]([CH:29]([NH:34][C:7](=[O:9])[C:6]1[CH:5]=[CH:4][C:3]([CH2:2][Br:1])=[CH:11][CH:10]=1)[CH2:30][CH:31]([CH3:32])[CH3:33])=[O:35])([CH3:26])[CH3:25])#[N:23]

Participants

5

Reactant 3

HCID 225994-(Bromomethyl)benzoic acidHCID 757711-HydroxybenzotriazoleHCID 539013662-Amino-4-methyl-pentanoic acid (cyano-dimethyl-methyl)-amide

Product 1

HCID 18316679HCID 18316679, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

4-Bromomethylbenzoic acid (4.1 mmol), HOBt (4.1 mmol) and WSCD.HCI (4.1 mmol) are dissolved in dimethylformamide (7 ml) and stirred for 10 min. 2-Amino-4-methyl-pentanoic acid (cyano-dimethyl-methyl)-amide (4.1 mmol) is added in DMF (3 ml) and the reaction mixture is stirred at RT overnight. After evaporation of the solvent, the residue is extracted with ethyl acetate. The extract is washed with water, 10% citric acid, brine, sodium bicarbonate, brine and dried over magnesium sulfate and evaporated. The crude product is suspended in diethylether and the solid filtered of and dried (vacuum). A white powder with mp. 185-187° C., Rf=0.43 (n-hexane:ethyl acetate=1:1) is obtained.

Workup

  1. stirringthe reaction mixture is stirred at RT overnight
  2. customAfter evaporation of the solvent
  3. extractionthe residue is extracted with ethyl acetate
  4. washThe extract is washed with water, 10% citric acid, brine, sodium bicarbonate, brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. filtrationthe solid filtered of and
  8. customdried (vacuum)
  9. customA white powder with mp. 185-187° C., Rf=0.43 (n-hexane:ethyl acetate=1:1) is obtained

Sources & evidence

ORD record
ord-3519902a1dbb48f2b0966711c6a79c4f
Source dataset
uspto-grants-2002_03
Patent number
US06353017B1

Reaction notes

Loading…