2-Phenylbutyric Acid → HCID 19102936, compound

HRID 1198612Notes

Reaction equation

HRID 1198612 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[C:16]1([CH:22]([CH2:26][CH3:27])[C:23]([OH:25])=[O:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O[N:29]1[C:33](=[O:34])[CH2:32][CH2:31][C:30]1=[O:35]>O1CCOCC1>[C:16]1([CH:22]([CH2:26][CH3:27])[C:23]([O:25][CH:31]2[CH2:32][C:33](=[O:34])[NH:29][C:30]2=[O:35])=[O:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 70122-Phenylbutyric AcidHCID 10868DicyclohexylcarbodiimideHCID 80170N-Hydroxysuccinimide

Product 1

HCID 19102936HCID 19102936, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of dicyclohexylcarbodiimide (6.91 g, 0.033 mol) in 33 mL of dry dioxane was added to a solution of 2-phenylbutyric acid (5.00 g, 0.030 mol) and N-hydroxysuccinimide (3.86 g, 0.034 mol) and the resulting mixture was allowed to stir overnight. The precipitated dicyclohexylurea by-product was filtered off and the filtrate concentrated under vacuum. The residue was dissolved in 5 mL of methylene chloride and filtered to remove a small amount of additional urea by-product. The solution was evaporated to give a white solid which was recrystallized from methanol to give 5.17 g (65%) of the product as white crystals; mp 96.5°-97.5° C.; 1H NMR (CDCl3) δ 0.99 (t, 3 H, J=7.4 Hz), 1.85-2.00 (m, 1 H), 2.13-2.28 (m, 1 H), 2.72 (br s, 4 H), 3.78 (t, 1 H, J=7.6 Hz), 7.35 (s, 5 H); 13C NMR (CDCl3) δ 11.49, 25.30, 26.89, 50.25, 127.95, 128.18, 128.92, 136.90, 169.24, 169.62; Anal. Calcd for C14H15NO4 : C, 64.36; H, 5.79; N, 5.36. Found: C, 64.63; H, 5.84; N, 5.34.

Workup

  1. filtrationThe precipitated dicyclohexylurea by-product was filtered off
  2. concentrationthe filtrate concentrated under vacuum
  3. dissolutionThe residue was dissolved in 5 mL of methylene chloride
  4. filtrationfiltered
  5. customto remove a small amount of additional urea by-product
  6. customThe solution was evaporated
  7. customto give a white solid which
  8. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-ed46a6da94344312ab5741cd98a6d3a3
Source dataset
uspto-grants-1994_01
Patent number
US05281617

Reaction notes

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