Trityl chloride → HCID 22219493, compound

HRID 1897528Notes

Reaction equation

HRID 1897528 reaction equation
Cl[C:2]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CCN(CC)CC.[NH:28]1[C:32]([CH2:33][C:34]([OH:36])=[O:35])=[N:31][N:30]=[N:29]1>C1COCC1.CCOC(C)=O>[C:2]([N:28]1[C:32]([CH2:33][C:34]([OH:36])=[O:35])=[N:31][N:30]=[N:29]1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 178525261HCID 178525261, compound

Product 1

HCID 22219493HCID 22219493, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

In an argon atmosphere, TrCl (936 mg, 3 mmol) and Et3N (556 μL, 3 mmol) were added to a solution of 1H-tetrazole-5-acetic acid (128 mg, 1 mmol) in THF (10 mL) and stirred for 3 hours at room temperature. The reaction mixture was diluted with EtOAc, and the organic layer was washed with water and dried over anhydrous sodium sulfate. The solution was filtered, and the filtrate was concentrated at a reduced pressure. The resulting residue was purified by neutral flash silica gel column chromatography (1.5×6, MeOH in CH2Cl2 0-0.5%) to give 2-(1-trityl-1H-tetrazol-5-yl)acetic acid (62 mg, 18%) as a white solid.

Workup

  1. washthe organic layer was washed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationThe solution was filtered
  4. concentrationthe filtrate was concentrated at a reduced pressure
  5. customThe resulting residue was purified by neutral flash silica gel column chromatography (1.5×6, MeOH in CH2Cl2 0-0.5%)

Sources & evidence

ORD record
ord-1b5aa27221044ebe9ab14674c218fe4a
Source dataset
uspto-grants-2013_08
Patent number
US08519128B2

Reaction notes

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