1,1'-Carbonyldiimidazole → HCID 59909769, compound

HRID 2183008Notes

Reaction equation

HRID 2183008 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.O[N:35]=[C:36]([NH2:40])[CH:37]([CH3:39])[CH3:38]>ClCCl>[CH:15]1([CH2:14][CH2:13][CH2:12][C@@H:8]([C:9]2[O:11][N:40]=[C:36]([CH:37]([CH3:39])[CH3:38])[N:35]=2)[CH2:7][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:21])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 2794833N'-Hydroxy-2-methylpropanimidamideHCID 9835906(2R)-2-[2-(tert-butoxy)-2-oxoethyl]-5-cyclohexylpentanoic acid

Product 1

HCID 59909769HCID 59909769, compoundYield 40.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (2R)-2-[2-(tert-butoxy)-2-oxoethyl]-5-cyclohexylpentanoic acid (Preparation 1) (500 mg, 1.70 mmol) in dichloromethane (30 ml) was treated with 1,1′-carbonyldiimidazole (272 mg, 1.70 mol) and the solution was stirred at room temperature for 1 hour. The N′-hydroxy-2-methylpropanimidamide (Monatsh.Chem.; 113; 1982; 781-792) (174 mg, 1.70 mmol) was then added and the mixture was stirred for 30 minutes. The solvent was removed under reduced pressure and the residue was heated neat at 120° C. under a nitrogen atmosphere for 18 hours. The crude product was then purified by column chromatography on silica gel eluting with dichloromethane to afford the title compound as a colourless oil (250 mg).

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. customThe solvent was removed under reduced pressure
  3. temperaturethe residue was heated neat at 120° C. under a nitrogen atmosphere for 18 hours
  4. customThe crude product was then purified by column chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-b7cb078a02b24bc4bddacd86292a9053
Source dataset
uspto-grants-2005_05
Patent number
US06897306B2

Reaction notes

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