Water → HCID 22405527, compound

HRID 1793947Notes

Reaction equation

HRID 1793947 reaction equation
[NH:1]1[C:5]([CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[N:4][N:3]=[N:2]1.C(N(CC)CC)C.[C:19](Cl)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>O1CCCC1>[C:19]([N:4]1[C:5]([CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[N:1][N:2]=[N:3]1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 178470801HCID 178470801, compound

Product 1

HCID 22405527HCID 22405527, compoundYield 51.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of 0.969 g of ethyl (1H-tetrazol-5-yl)acetate in 9mL of tetrahydrofuran were added successively 0.932 mL of triethylamine and 1.68 g of trityl chloride at room temperature, and the mixture was stirred at the same temperature for 2 hours. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, and 1 mol/L hydrochloric acid, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: ethyl acetate-hexane) to give 1.23 g of ethyl (1-trityl-1H-tetrazol-5-yl)acetate.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water, and 1 mol/L hydrochloric acid
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel (eluent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-24fa5c7d686b43718123dc0ad3a18155
Source dataset
uspto-grants-2006_04
Patent number
US07022689B2

Reaction notes

Loading…