Water → 4-Cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [2-cyclohex-1-enyl-4-(2-hydroxy-1-hydroxymethyl-ethyl)-phenyl]-amide

HRID 408928Notes

Reaction equation

HRID 408928 reaction equation
C([O:4][CH2:5][CH:6]([C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]([C:21]2[N:22]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])[CH:23]=[C:24]([C:26]#[N:27])[N:25]=2)=[O:20])=[C:14]([C:36]2[CH2:41][CH2:40][CH2:39][CH2:38][CH:37]=2)[CH:13]=1)[CH2:7][O:8]C(=O)C)(=O)C.[OH-].[Na+].C(Cl)Cl.O>CC(O)C>[C:36]1([C:14]2[CH:13]=[C:12]([CH:6]([CH2:5][OH:4])[CH2:7][OH:8])[CH:17]=[CH:16][C:15]=2[NH:18][C:19]([C:21]2[N:22]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:33])([CH3:35])[CH3:34])[CH:23]=[C:24]([C:26]#[N:27])[N:25]=2)=[O:20])[CH2:41][CH2:40][CH2:39][CH2:38][CH:37]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 59771165Acetic acid 3-acetoxy-2-(4-{[4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carbonyl]-amino}-3-cyclohex-1-enyl-phenyl)-propyl ester

Product 1

HCID 597712694-Cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [2-cyclohex-1-enyl-4-(2-hydroxy-1-hydroxymethyl-ethyl)-phenyl]-amideYield 63%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of acetic acid 3-acetoxy-2-(4-{[4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carbonyl]-amino}-3-cyclohex-1-enyl-phenyl)-propyl ester (as prepared in the previous step, 580 mg, 1.00 mmol) in i-PrOH (15 mL), 2N NaOH (1 mL, 2 mmol) was added. The reaction mixture was stirred at RT for 1 h, and DCM (200 mL) and water (200 mL) were added. The organic layer was separated, dried (Na2SO4) and concentrated. The residue was purified on silica (40% EtOAc-hexane) to obtain the title compound (312 mg, 63%): Mass spectrum (ESI, m/z): Calcd. for C26H36N4O4Si, 497.2 (M+H). found 497.0.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was purified on silica (40% EtOAc-hexane)

Sources & evidence

ORD record
ord-26c3824efa1746448c6332caaf49ccbb
Source dataset
uspto-grants-2014_06
Patent number
US08759347B2

Reaction notes

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