Acetic Acid → 3-{4-[(4-bromophenylamino)methyl]benzoylamino}propionic Acid

HRID 1633966Notes

Reaction equation

HRID 1633966 reaction equation
[CH:1]([C:3]1[CH:16]=[CH:15][C:6]([C:7]([NH:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[O:8])=[CH:5][CH:4]=1)=O.[Br:17][C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1.C(O)(=O)C.C([BH3-])#N.[Na+]>CN(C=O)C.COC(OC)OC>[Br:17][C:18]1[CH:24]=[CH:23][C:21]([NH:22][CH2:1][C:3]2[CH:16]=[CH:15][C:6]([C:7]([NH:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[O:8])=[CH:5][CH:4]=2)=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 78074-BromoanilineHCID 5003444Sodium cyanoborohydrideHCID 225023533-(4-Formylbenzamido)propanoic acid

Product 1

HCID 225018703-{4-[(4-bromophenylamino)methyl]benzoylamino}propionic Acid

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 9005Trimethyl orthoformateSolvent2×

Procedure

The above resin bound 3-(4-formylbenzoylamino)propionic acid (50 mg) was treated with a solution of 4-bromoaniline (500 [mol) in a mixture of DMF (500 μL) and trimethylorthoformate (500 μL). Glacial acetic acid (100 μL) was added and the mixture was shaked for 1 hour at 25° C. Sodium cyanoborohydride (750 μmol) suspended in a mixture of DMF and trimethyl-orthoformate (1:1, 1 mL) was added and the mixture was vortexed at 25° C. for 16 hours followed by filtration and washing with a mixture of DMF and water (4:1, 2×1 mL) followed by 3×1 mL DMF and 2×1 mL dichloromethane to afford the desired product.

Workup

  1. additionwas added
  2. waitthe mixture was vortexed at 25° C. for 16 hours
  3. filtrationfollowed by filtration
  4. washwashing with a mixture of DMF and water (4:1, 2×1 mL)

Sources & evidence

ORD record
ord-a4d0038d7a064627bc17dc4b5dc928d6
Source dataset
uspto-grants-2003_01
Patent number
US06503949B1

Reaction notes

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