Ethyl Acetate → HCID 178424502, compound

HRID 1190220Notes

Reaction equation

HRID 1190220 reaction equation
[CH3:1][C:2]1([CH3:29])[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]([CH3:18])([CH3:17])[CH2:15][OH:16])[CH:11]=[CH:10][C:9]=2[NH:19][C:20]([C:22]2[NH:23][CH:24]=[C:25]([C:27]#[N:28])[N:26]=2)=[O:21])=[CH:4][CH2:3]1.C([O-])(O)=O.[Na+].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.CCOC(C)=O>C(Cl)Cl>[CH3:1][C:2]1([CH3:29])[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]([CH3:17])([CH3:18])[CH:15]=[O:16])[CH:11]=[CH:10][C:9]=2[NH:19][C:20]([C:22]2[NH:23][CH:24]=[C:25]([C:27]#[N:28])[N:26]=2)=[O:21])=[CH:4][CH2:3]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 178424503HCID 178424503, compound

Product 1

HCID 178424502HCID 178424502, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 4-cyano-1H-imidazole-2-carboxylic acid [2-(4,4-dimethyl-cyclohex-1-enyl)-4-(2-hydroxy-1,1-dimethyl-ethyl)-phenyl]-amide (as prepared in the previous step, 1.00 g, 2.55 mmol) and NaHCO3 (1.07 g, 12.8 mmol) in 40 mL of DCM at 0° C. was added Dess-Martin periodinane (Adv. Syn. Chem., 2004, 346, 111-124, 2.16 g, 5.10 mmol). After stirring at 0° C. for 0.5 h, the reaction was warmed to RT and continued to stir for 2 h. The mixture was treated with 100 mL of EtOAc and washed with 10% aqueous Na2S2O3 (2×20 mL), aqueous saturated NaHCO3 (20 mL), H2O (20 mL) and brine (10 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was purified by silica gel chromatography (0-3% MeOH/DCM) to afford the title compound (876 mg, 88%) as a white solid. Mass spectrum (ESI, m/z): Calcd. for C23H26N4O2, 391.2 (M+H). found 391.1.

Workup

  1. temperaturethe reaction was warmed to RT
  2. stirringto stir for 2 h
  3. washwashed with 10% aqueous Na2S2O3 (2×20 mL), aqueous saturated NaHCO3 (20 mL), H2O (20 mL) and brine (10 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography (0-3% MeOH/DCM)

Sources & evidence

ORD record
ord-7fdaa7ab931e472f96a0e72ceb88669c
Source dataset
uspto-grants-2014_03
Patent number
US08674100B2

Reaction notes

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