Dimethyl Sulfoxide → 5-[4'-(5-Azidomethyl-2-butyl-4-chloro-imidazol-1-ylmethyl)-biphenyl-2-yl]-1-trityl-1H-tetrazole

HRID 1472263Notes

Reaction equation

HRID 1472263 reaction equation
CS(C)=O.[CH2:5]([C:9]1[N:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]3[N:31]([C:32]([C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[N:30]=[N:29][N:28]=3)=[CH:17][CH:16]=2)[C:12]([CH2:51]OS(C)(=O)=O)=[C:11]([Cl:57])[N:10]=1)[CH2:6][CH2:7][CH3:8].[N-:58]=[N+:59]=[N-:60].[Na+].[Na+].[Cl-]>CCOC(C)=O>[N:58]([CH2:51][C:12]1[N:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]3[N:31]([C:32]([C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[N:30]=[N:29][N:28]=3)=[CH:17][CH:16]=2)[C:9]([CH2:5][CH2:6][CH2:7][CH3:8])=[N:10][C:11]=1[Cl:57])=[N+:59]=[N-:60]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 5234Sodium ChlorideHCID 33557Sodium AzideHCID 86624363Methanesulfonic acid 2-butyl-5-chloro-3-[2'-(1-trityl-1H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-3H-imidazol-4-ylmethyl ester

Product 1

HCID 866262645-[4'-(5-Azidomethyl-2-butyl-4-chloro-imidazol-1-ylmethyl)-biphenyl-2-yl]-1-trityl-1H-tetrazoleYield 86.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a dimethyl sulfoxide (100 mL) solution of intermediate (11c) (15 g, 20 mmol) was added sodium azide (3.9 g, 60 mmol). The mixture was stirred at room temperature for 20 minutes. EtOAc (500 mL) and saturated aqueous NaCl (100 mL) were added and the layers were separated, retaining the organic layer. The organic was washed an additional three times with saturated aqueous NaCl (100 mL). After drying over sodium sulfate and filtration, the removal of solvent provided intermediate (11d) as a yellow solid (12 g), which was used directly in the next step. MS m/z: [M+H+] calcd for C41H36ClN9, 690.29; found 690.5.

Workup

  1. customthe layers were separated
  2. washThe organic was washed an additional three times with saturated aqueous NaCl (100 mL)
  3. dry with materialAfter drying over sodium sulfate and filtration
  4. customthe removal of solvent

Sources & evidence

ORD record
ord-2606265f2c074f34a52fe77ae1db183b
Source dataset
uspto-grants-2015_04
Patent number
US09012485B2

Reaction notes

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