Dicyclohexylcarbodiimide → 4-Butyl-2-phenyl-1,3-oxazol-5(4H)-one

HRID 1252161Notes

Reaction equation

HRID 1252161 reaction equation
[C:1]([NH:9][CH:10]([C:15]([OH:17])=[O:16])[CH2:11][CH2:12][CH2:13][CH3:14])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[C:2]1([C:1]2[O:17][C:15](=[O:16])[CH:10]([CH2:11][CH2:12][CH2:13][CH3:14])[N:9]=2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 328208N-Benzoylnorleucine

Product 1

HCID 141299024-Butyl-2-phenyl-1,3-oxazol-5(4H)-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

N-(Benzoyl)-D,L-norleucine (40 g., 170 mmole) is taken into 300 ml. of tetrahydrofuran with stirring in an ice bath. To this is added dropwise dicyclohexylcarbodiimide (38.52 g., 187 mmole) in tetrahydrofuran (195 ml.). After 15 minutes the bath is removed and the reaction is allowed to run overnight. The dicyclohexylurea is filtered off and the filtrate is concentrated to dryness. The crude product (31.7 g.) is purified on silica gel in hexane:ether (2:1) to give 2-phenyl-4-butyl-5(4H)-oxazolone. This product crystallizes neat when refrigerated.

Workup

  1. customAfter 15 minutes the bath is removed
  2. filtrationThe dicyclohexylurea is filtered off
  3. concentrationthe filtrate is concentrated to dryness
  4. customThe crude product (31.7 g.) is purified on silica gel in hexane:ether (2:1)

Sources & evidence

ORD record
ord-e9f080efb6bd44278ffec0b91f6802a2
Source dataset
uspto-grants-1988_05
Patent number
US04742067

Reaction notes

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