Hippuric Acid → HCID 14626423, compound

HRID 1602737Notes

Reaction equation

HRID 1602737 reaction equation
[C:1]([OH:13])(=O)[CH2:2][NH:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[NH2:14][C@H:15]([C:20]([OH:22])=[O:21])[CH2:16][C:17]([OH:19])=[O:18].C(N(CC)CC)C.O>CN(C=O)C>[C:1]([NH:14][C@H:15]([C:20]([OH:22])=[O:21])[CH2:16][C:17]([OH:19])=[O:18])(=[O:13])[CH2:2][NH:3][C:4]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)=[O:5]

Participants

6

Reactant 4

HCID 464Hippuric AcidHCID 962WaterHCID 5960L-Aspartic AcidHCID 8471Triethylamine

Product 1

HCID 14626423HCID 14626423, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The starting material was synthesised as follows. To a solution of hippuric acid (0.90 g, 5×10-3 moles) and L-aspartic acid dibenyzl ester (2.31 g, 5×10-3 moles) in DMF (35 ml) was added 1-hyhdroxybenzotriazole (0.73 g, 5.5×10-3 moles), triethylamine (1.4 ml, 9.7×10-3 moles) and 1-(3-dimethyl-aminopropyl)-3-ethylcarbodiimide, HCl salt (1.05 g, 5.5×10-3 moles). The mixture was stirred for 4 hours at room temperature then poured into water (450 ml) and extracted twice with ethyl acetate (100 ml). The extract was washed with saturated sodium bicarbonate solution, water, 2N HCl and water. The organic phase was dried over MgSO4 and evaporated to dryness to obtain the desired starting material as a yellow oil. 1.90 g (80%)

Workup

  1. customThe starting material was synthesised
  2. extractionextracted twice with ethyl acetate (100 ml)
  3. washThe extract was washed with saturated sodium bicarbonate solution, water, 2N HCl and water
  4. dry with materialThe organic phase was dried over MgSO4
  5. customevaporated to dryness
  6. customto obtain the

Sources & evidence

ORD record
ord-6e4dfd5a61154ce48ee6246bbcf7e5a5
Source dataset
uspto-grants-1999_11
Patent number
US05985281

Reaction notes

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