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2-Trityl-5-methyl tetrazole → N-(2,4-dimethylphenyl)-4-(2-hydroxy-1-(2-trityl-2H-tetrazol-5-yl)propan-2-yl)-N-isobutylbenzenesulfonamide

HRID 1746439
Notes
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Reaction equation

HRID 1746439 reaction equation
[CH3:1][C:2]1[N:3]=[N:4][N:5]([C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:6]=1.[Li]CCCC.[C:31]([C:34]1[CH:39]=[CH:38][C:37]([S:40]([N:43]([C:48]2[CH:53]=[CH:52][C:51]([CH3:54])=[CH:50][C:49]=2[CH3:55])[CH2:44][CH:45]([CH3:47])[CH3:46])(=[O:42])=[O:41])=[CH:36][CH:35]=1)(=[O:33])[CH3:32]>O1CCCC1>[CH3:55][C:49]1[CH:50]=[C:51]([CH3:54])[CH:52]=[CH:53][C:48]=1[N:43]([CH2:44][CH:45]([CH3:47])[CH3:46])[S:40]([C:37]1[CH:38]=[CH:39][C:34]([C:31]([OH:33])([CH3:32])[CH2:1][C:2]2[N:3]=[N:4][N:5]([C:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:6]=2)=[CH:35][CH:36]=1)(=[O:42])=[O:41]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 109583602-Trityl-5-methyl tetrazoleHCID 867316024-acetyl-N-(2,4-dimethylphenyl)-N-isobutylbenzenesulfonamideHCID 178418339Butyllithium2×

Product 1

HCID 86731603N-(2,4-dimethylphenyl)-4-(2-hydroxy-1-(2-trityl-2H-tetrazol-5-yl)propan-2-yl)-N-isobutylbenzenesulfonamideYield 15.3%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
3×

Conditions

Temperature
-78 °C

Procedure

To a solution of 5-methyl-2-trityl-2H-tetrazole (68.5 mg, 0.21 mmol) in tetrahydrofuran (THF) (1 mL) stirred under nitrogen at −70° C., was added a solution of n-BuLi (1.6 M in hexanes, 0.144 mL, 0.231 mmol) and tetrahydrofuran (THF) (1 mL) dropwise over 1 minute. The reaction mixture was stirred at −78° C. for 45 minutes, then 4-acetyl-N-(2,4-dimethylphenyl)-N-isobutylbenzenesulfonamide (106 mg, 0.294 mmol) in tetrahydrofuran (THF) (1 mL) was added dropwise at −78° C. over 1 minute. The reaction mixture was stirred at −78° C. for 1 hour, then allowed to warm to room temperature. The reaction was carefully quenched using a few drops of water under nitrogen. Ethyl acetate (3 mL) and water (2 mL) were then added and the reaction stirred vigorously for 5 minutes. The organic phase was separated using a hydrophilic frit and concentrated in vacuo to give a residue. LCMS analysis showed incomplete reaction, so the above reaction procedure repeated using fresh n-butyl lithium solution and reintroducing the crude residue instead of new starting material, this resulted in improved conversion. The residue was then purified by flash silica (Si) chromatography (using a 0-25% ethyl acetate-cyclohexane gradient) to give the required product (22 mg) as a colourless gum. LCMS (M+1) 686, RT 1.57 mins.

Workup

  1. stirringThe reaction mixture was stirred at −78° C. for 1 hour
  2. temperatureto warm to room temperature
  3. customThe reaction was carefully quenched
  4. additionEthyl acetate (3 mL) and water (2 mL) were then added
  5. stirringthe reaction stirred vigorously for 5 minutes
  6. customThe organic phase was separated
  7. concentrationconcentrated in vacuo
  8. customto give a residue
  9. customreaction
  10. customso the above reaction procedure
  11. customthis resulted in improved conversion
  12. customThe residue was then purified by flash silica (Si) chromatography (

Sources & evidence

ORD record
ord-f6542f80d2ba410786baece8f1140b51
Source dataset
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09150508B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes