(4-chloro-phenyl)-{4-[hydroxy-(1-trityl-1H-imidazol-4-yl)-methyl]-1-methyl-1H-pyrrol-2-yl}methanone → (4-chlorophenyl)-[1-methyl-4-(1-trityl-1H-imidazole-4-carbonyl)-1H-pyrrol-2-yl]methanone

HRID 2182819

Reaction equation

HRID 2182819 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[N:11]([CH3:41])[CH:12]=[C:13]([CH:15]([OH:40])[C:16]3[N:17]=[CH:18][N:19]([C:21]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH:20]=3)[CH:14]=2)=[O:9])=[CH:4][CH:3]=1>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[N:11]([CH3:41])[CH:12]=[C:13]([C:15]([C:16]3[N:17]=[CH:18][N:19]([C:21]([C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)([C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=4)[C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH:20]=3)=[O:40])[CH:14]=2)=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 22481044(4-chloro-phenyl)-{4-[hydroxy-(1-trityl-1H-imidazol-4-yl)-methyl]-1-methyl-1H-pyrrol-2-yl}methanone

Product 1

HCID 22481054(4-chlorophenyl)-[1-methyl-4-(1-trityl-1H-imidazole-4-carbonyl)-1H-pyrrol-2-yl]methanoneYield 91.2%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution 2.2 g of (4-chloro-phenyl)-{4-[hydroxy-(1-trityl-1H-imidazol-4-yl)-methyl]-1-methyl-1H-pyrrol-2-yl}methanone in 50 mL of CH2Cl2 was stirred with 2.5 g of activated manganese dioxide overnight. The reaction was filtered and the filtrate was evaporated in vacuo to give 2.0 g of (4-chlorophenyl)-[1-methyl-4-(1-trityl-1H-imidazole-4-carbonyl)-1H-pyrrol-2yl]methanone. CI-MS m/z=556 (M++H).

Workup

  1. filtrationThe reaction was filtered
  2. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-ee6f703721df4b17a9b06c3a10cdb866
Source dataset
uspto-grants-2005_05
Patent number
US06897319B2

Linked notes

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