Hippuric Acid → HCID 14626423, compound

HRID 2304367Notes

Reaction equation

HRID 2304367 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].C([O:21][C:22](=[O:36])[C@H:23]([CH2:25][C:26]([O:28]CC1C=CC=CC=1)=[O:27])[NH2:24])C1C=CC=CC=1.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C=O)C.O>[C:1]([NH:24][C@H:23]([C:22]([OH:36])=[O:21])[CH2:25][C:26]([OH:28])=[O:27])(=[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

7

Reactant 4

HCID 464Hippuric AcidHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 2808532Dibenzyl L-aspartate

Product 1

HCID 14626423HCID 14626423, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 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 dibenzyl ester (2.31 g, 5×10−3 moles) in DMF (35 ml) was added 1-hydroxybenzotriazole (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-0fd1f2ef19bd45af8c7c0c926aae33ca
Source dataset
uspto-grants-2002_08
Patent number
US06436691B1

Reaction notes

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