Trityl chloride → 2-[4-Hydroxyphenyl]-1-cyclohexyl-5-[2-(trityl)-2h-tetrazol-5-yl]-1h-benzimidazole

HRID 392968Notes

Reaction equation

HRID 392968 reaction equation
[C:1](Cl)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[Si]([O:37][C:38]1[CH:43]=[CH:42][C:41]([C:44]2[N:48]([CH:49]3[CH2:54][CH2:53][CH2:52][CH2:51][CH2:50]3)[C:47]3[CH:55]=[CH:56][C:57]([C:59]4[NH:63][N:62]=[N:61][N:60]=4)=[CH:58][C:46]=3[N:45]=2)=[CH:40][CH:39]=1)(C(C)(C)C)(C)C.C(OCC)(=O)C>CN(C=O)C.O>[OH:37][C:38]1[CH:39]=[CH:40][C:41]([C:44]2[N:48]([CH:49]3[CH2:54][CH2:53][CH2:52][CH2:51][CH2:50]3)[C:47]3[CH:55]=[CH:56][C:57]([C:59]4[N:60]=[N:61][N:62]([C:1]([C:14]5[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=5)([C:8]5[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=5)[C:2]5[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=5)[N:63]=4)=[CH:58][C:46]=3[N:45]=2)=[CH:42][CH:43]=1

Participants

7

Reactant 4

HCID 6456Trityl chlorideHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 226608122-[4-(tert-Butyldimethylsilyoxy)phenyl]-1-cyclohexyl-5-(1H-tetrazol-5-yl)-1H-benzimidazole

Product 1

HCID 1356740972-[4-Hydroxyphenyl]-1-cyclohexyl-5-[2-(trityl)-2h-tetrazol-5-yl]-1h-benzimidazoleYield 96.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Trityl chloride (4.57 g, 0.0164 mol) and N,N-diisopropylethylamine (2.42 g, 0.0187 mol) were added to a stirred mixture of compound 21 (7.4 g, 0.0156 mol) in DMF (36 mL). The mixture was stirred for 18 h at an oil bath temperature of 70° C. The mixture was cooled and poured into a mixture of ethyl acetate and water to precipitate the fully protected benzimidazole, 2-[4-(tert-butyldimethylsilyoxy)phenyl]-1-cyclohexyl-5-[2-(trityl)-2H-tetrazol-5-yl]-1H-benzimidazole. The solid was collected, washed with cold water and dried to afford the protected benzimidazole as a colorless solid (9.1 g, 81% yield). ESI-MS m/e 717 (M+1). HPLC purity (uv) 94%.

Workup

  1. temperatureThe mixture was cooled
  2. customto precipitate the fully protected benzimidazole, 2-[4-(tert-butyldimethylsilyoxy)phenyl]-1-cyclohexyl-5-[2-(trityl)-2H-tetrazol-5-yl]-1H-benzimidazole
  3. customThe solid was collected
  4. washwashed with cold water
  5. customdried

Sources & evidence

ORD record
ord-879266e25a0a415292486745dca0167f
Source dataset
uspto-grants-2004_10
Patent number
US06803374B2

Reaction notes

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