2-butyl-1-[(2'-t-butoxycarbonylbiphen-4-yl)methyl]-5-chloro-1H-imidazole-4-methanol → 2-Butyl-1-[(2'-t-butoxycarbonylbiphen-4-yl)-methyl]-5-chloro-1H-imidazole-4-carboxaldehyde

HRID 373611Notes

Reaction equation

HRID 373611 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[CH:16][CH:15]=2)[C:7]([Cl:12])=[C:8]([CH2:10][OH:11])[N:9]=1)[CH2:2][CH2:3][CH3:4]>C(Cl)Cl.O=[Mn]=O>[CH2:1]([C:5]1[N:6]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]([O:28][C:29]([CH3:30])([CH3:32])[CH3:31])=[O:27])=[CH:16][CH:15]=2)[C:7]([Cl:12])=[C:8]([CH:10]=[O:11])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 1317176442-butyl-1-[(2'-t-butoxycarbonylbiphen-4-yl)methyl]-5-chloro-1H-imidazole-4-methanol

Product 1

HCID 1317176432-Butyl-1-[(2'-t-butoxycarbonylbiphen-4-yl)-methyl]-5-chloro-1H-imidazole-4-carboxaldehydeYield 0.1%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-butyl-1-[(2'-t-butoxycarbonylbiphen-4-yl)methyl]-5-chloro-1H-imidazole-4-methanol (European Patent Applications 253,310) (145 mg, 319 mmol), MnO2 (550 mg, 6.4 mmol), 3A powdered sieves (500 mg) in CH2Cl2 (10 mL) was stirred at room temperature for 3 hours. The mixture was filtered and evaporated to give 142 mg of the title compound as a glass. 1H NMR (300 MHz, CD3OD)δ 9.82 (s, 1H), 7.70 (dd, 1H, J=7 and 1.5 Hz), 7.50 (td, 1H, J=7 and 1.5 Hz), 7.40 (td, 1H, J=7 and 1.5 Hz), 7.31-7.26 (m, 3H), 7.15 (apparent d, 2H, J=3 Hz), 5.38 (s, 2H), 2.73 (t, 2H, J=7.5 Hz), 1.72-1.62 (m, 2H), 1.45-1.30 (m, 2H) 1.21 (s, 9H), 0.90 (t, 3H, J=7 Hz).

Workup

  1. filtrationThe mixture was filtered
  2. customevaporated

Sources & evidence

ORD record
ord-52871769f9c54a408e328f1813ea90ee
Source dataset
uspto-grants-1992_11
Patent number
US05164407

Reaction notes

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