Hippuric Acid → HCID 13649253, compound

HRID 1200148Notes

Reaction equation

HRID 1200148 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[NH2:16][CH:17]([CH3:22])[C:18]([CH3:21])([CH3:20])[CH3:19].[C:23](O)(=[O:34])[CH2:24][NH:25][C:26]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:27]>C(OCC)(=O)C>[CH3:22][CH:17]([NH:16][C:23](=[O:34])[CH2:24][NH:25][C:26](=[O:27])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:18]([CH3:21])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 464Hippuric AcidHCID 10868DicyclohexylcarbodiimideHCID 5209072-Butanamine, 3,3-dimethyl-

Product 1

HCID 13649253HCID 13649253, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2.2 g of dicyclohexylcarbodiimide were added to 30 ml of an ethyl acetate solution containing 1.0 g of 3-amino-2,2-dimethylbutane and 1.7 g of hippuric acid in an ice bath. The reaction solution was stirred for 2 hours at room temperature and then allowed to stand overnight. The solid material which separated was filtered off, after which the filtrate was washed with a 10% w/v aqueous solution of sodium hydroxide, then with 1N aqueous hydrochloric acid, and finally with a saturated aqueous sodium chloride solution. It was then dried over anhydrous sodium sulfate. The reaction solution was concentrated by evaporation under reduced pressure, and the resulting residue was purified by silica gel column chromatography to give 1.65 g (yield 64%) of the title product melting at 124°-126° C.

Workup

  1. waitto stand overnight
  2. customThe solid material which separated
  3. filtrationwas filtered off
  4. washafter which the filtrate was washed with a 10% w/v aqueous solution of sodium hydroxide
  5. dry with materialIt was then dried over anhydrous sodium sulfate
  6. concentrationThe reaction solution was concentrated by evaporation under reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-61fc216f9b7e4651a09e4c943a1c6609
Source dataset
uspto-grants-1990_02
Patent number
US04904680

Reaction notes

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