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

HRID 1633968Notes

Reaction equation

HRID 1633968 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.[CH2:17]([O:21][C:22]1[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=1)[CH2:18][CH2:19][CH3:20].C(O)(=O)C.C([BH3-])#N.[Na+]>CN(C=O)C.COC(OC)OC.CO>[CH2:17]([O:21][C:22]1[CH:23]=[CH:24][C:25]([NH:26][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:27][CH:28]=1)[CH2:18][CH2:19][CH3:20]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 203524-ButyloxyanilineHCID 5003444Sodium cyanoborohydrideHCID 225023533-(4-Formylbenzamido)propanoic acid

Product 1

HCID 225020713-{4-[(4-Butoxyphenylamino)methyl]benzoylamino}propionic Acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent2×HCID 9005Trimethyl orthoformateSolvent

Procedure

The above resin bound 3-(4-formylbenzoylamino)propionic acid (50 mg) was treated with a 0.5 M solution of 4-butoxyaniline (0.25 mmol, 41.25 mg) in a mixture of DMF and trimethylorthoformate (1:1, 0.5 mL) and glacial acetic acid (50 μL) for 1 hour at 25° C. Sodium cyanoborohydride (250 μmol, 16 mg) dissolved in a mixture of DMF and methanol (1:1, 0.25 mL) was added, and the mixture was vortexed at 25° C. for 4 hours followed by filtration and washing with a mixture of DMF and methanol (1:1, 2×1 mL) 3×1 mL DMF and 2×1 mL dichloromethane to afford the desired product.

Workup

  1. additionwas added
  2. filtrationfollowed by filtration
  3. washwashing with a mixture of DMF and methanol (1:1, 2×1 mL) 3×1 mL DMF and 2×1 mL dichloromethane

Sources & evidence

ORD record
ord-df1850029fba4020af144e2bccbae546
Source dataset
uspto-grants-2003_01
Patent number
US06503949B1

Reaction notes

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