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

HRID 1731397Notes

Reaction equation

HRID 1731397 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-5a1c6f7f62e1469384289b947f99efd8
Source dataset
uspto-grants-1986_11
Patent number
US04621092

Reaction notes

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