1,1'-Carbonyldiimidazole → HCID 59909802, compound

HRID 1279854Notes

Reaction equation

HRID 1279854 reaction equation
[C:1]([O:5][C:6](=[O:21])[CH2:7][C@@H:8]([CH2:12][CH2:13][CH2:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[C:9]([OH:11])=O)([CH3:4])([CH3:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[Cl:34][C:35]1[CH:46]=[CH:45][C:38]([O:39][CH2:40][C:41](=[N:43]O)[NH2:42])=[CH:37][CH:36]=1>ClCCl>[Cl:34][C:35]1[CH:36]=[CH:37][C:38]([O:39][CH2:40][C:41]2[N:43]=[C:9]([C@H:8]([CH2:12][CH2:13][CH2:14][CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)[CH2:7][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:21])[O:11][N:42]=2)=[CH:45][CH:46]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 53592579295-18-4HCID 9835906(2R)-2-[2-(tert-butoxy)-2-oxoethyl]-5-cyclohexylpentanoic acid

Product 1

HCID 59909802HCID 59909802, compoundYield 48.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (2R)-2-[2-(tert-butoxy)-2-oxoethyl]-5-cyclohexylpentanoic acid (Preparation 1) (300 mg, 1.00 mmol) in dichloromethane (15 ml) was treated with 1,1′-carbonyldiimidazole (162 mg, 1.00 mmol) and the solution was stirred at room temperature for 2 hours. 2-(4-chlorophenoxy)-N′-hydroxyethanimidamide (Patent US 97-815671 970313) (197 mg, 0.98 mmol) was then added and the mixture was stirred for 17 hours. The solvent was removed under reduced pressure and the residue was heated neat at 120° C. under a nitrogen atmosphere for 2 hours. The crude product was then purified by column chromatography on silica gel eluting with dichloromethane:methanol (99:1) to afford the title compound as a colourless oil (220 mg).

Workup

  1. stirringthe mixture was stirred for 17 hours
  2. customThe solvent was removed under reduced pressure
  3. temperaturethe residue was heated neat at 120° C. under a nitrogen atmosphere for 2 hours
  4. customThe crude product was then purified by column chromatography on silica gel eluting with dichloromethane:methanol (99:1)

Sources & evidence

ORD record
ord-6ca84cc5bb50451e8fc37f68139a6c26
Source dataset
uspto-grants-2002_09
Patent number
US06448278B2

Reaction notes

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