4-Phenylbutyric Acid → 1-[(4-Phenylbutanoyl)oxy]pyrrolidine-2,5-dione

HRID 1362578Notes

Reaction equation

HRID 1362578 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O[N:14]1[C:18](=[O:19])[CH2:17][CH2:16][C:15]1=[O:20].C1(N=C=NC2CCCCC2)CCCCC1>C(#N)C>[O:20]=[C:15]1[CH2:16][CH2:17][C:18](=[O:19])[N:14]1[O:11][C:10](=[O:12])[CH2:9][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 47754-Phenylbutyric AcidHCID 10868DicyclohexylcarbodiimideHCID 80170N-Hydroxysuccinimide

Product 1

HCID 139371181-[(4-Phenylbutanoyl)oxy]pyrrolidine-2,5-dioneYield 72%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(Method J15A) A solution of 4-phenyl-butyric acid (1/95) (6.570 g, 40 mmol) and N-hydroxysuccinimide (4.830 g, 42 mmol) in acetonitrile (100 ml) was treated with N,N′-dicyclohexylcarbodiimide (8.650 g, 42 mmol) at 0° C. The resulting suspension was allowed to stand for 14 hours at 4° C., the precipitate was filtered off and washed with ethyl acetate (3×30 ml). The solvents were removed in vacuum and the residue was crystallized from isopropanol (50 ml) to give the activated ester 15/95 (7.520 g, 72%) as colorless crystals. 1H NMR (DMSO-d6, HMDSO) δ: 1.78-2.20 (2H, m); 2.53-3.00 (8H, m); 6.84-7.67 (5H, m); 10.80 (1H, s).

Workup

  1. filtrationthe precipitate was filtered off
  2. washwashed with ethyl acetate (3×30 ml)
  3. customThe solvents were removed in vacuum
  4. customthe residue was crystallized from isopropanol (50 ml)

Sources & evidence

ORD record
ord-c9a56825c97e491193c1c74328733cd0
Source dataset
uspto-grants-2011_02
Patent number
US07880020B2

Reaction notes

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