Hippuric Acid → HCID 70171581, compound

HRID 1602736Notes

Reaction equation

HRID 1602736 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].[CH2:14]([O:21][C:22](=[O:37])[C@H:23]([CH2:25][CH2:26][C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28])[NH2:24])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C=O)C.O>[CH2:14]([O:21][C:22](=[O:37])[C@H:23]([CH2:25][CH2:26][C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28])[NH:24][C:1](=[O:13])[CH2:2][NH:3][C:4]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)=[O:5])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 464Hippuric AcidHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 3037947L-Glutamic acid dibenzyl ester

Product 1

HCID 70171581HCID 70171581, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The starting material compound 3 was prepared as follow. To a solution of hippuric acid (0.90 g, 5×10-3 moles) and L-glutamic acid dibenzyl ester (2.50 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 overnight at room temperature, poured into water (400 ml) and extracted twice with ethyl acetate (100 ml). The combined extracts were washed with saturated sodium bicarbonate solution, water, 2N HCl and water. The organic phase was dried over MgSO4 and evaporated to obtain the desired starting material as a yellow oil. 2.06 g (84%).

Workup

  1. extractionextracted twice with ethyl acetate (100 ml)
  2. washThe combined extracts were washed with saturated sodium bicarbonate solution, water, 2N HCl and water
  3. dry with materialThe organic phase was dried over MgSO4
  4. customevaporated
  5. customto obtain the

Sources & evidence

ORD record
ord-7aacca11244c4437b50936845219575e
Source dataset
uspto-grants-1999_11
Patent number
US05985281

Reaction notes

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