Water → (2-trityl-2H-tetrazol-5-yl)-acetic acid

HRID 643262Notes

Reaction equation

HRID 643262 reaction equation
C([O:3][C:4](=[O:11])[CH2:5][C:6]1[N:7]=[N:8][NH:9][N:10]=1)C.[C:12](Cl)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O.[OH-].[K+]>C1COCC1.C(O)C>[C:12]([N:8]1[N:9]=[N:10][C:6]([CH2:5][C:4]([OH:3])=[O:11])=[N:7]1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6456Trityl chlorideHCID 14797Potassium HydroxideHCID 543616Ethyl 1H-tetrazole-5-acetate

Product 1

HCID 22405503(2-trityl-2H-tetrazol-5-yl)-acetic acidYield 15%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of (2H-tetrazol-5-yl)-acetic acid ethyl ester (2.0 g, 12.81 mmol), trityl chloride (3.7 g, 13.45 mmol) in dry THF (75 ml) was added TEA (3.7 ml). The resulting mixture was stirred for 18 hrs. at room temperature. Water (10 ml) was added and the precipitate filtered off, redissolved in EtOAc (25 ml) and washed with saturated aqueous ammonium chloride (2×15 ml). The organic phase was dried (Na2SO4), filtered and evaporated in vacuo. The residue was suspended in ethanol (150 ml) and potassium hydroxide (0.8 g, 13.45 mmol) dissolved in ethanol (100 ml) was added. The resulting mixture was stirred for 18 hrs. at room temperature. The precipitate was filtered off and dissolved in water (150 ml) and acidified with conc. HCl (use diluted HCl). The precipitate was filtered off and washed with diethyl ether and dried in vacuo at 50° C. affording 0.7 g (15%) of (2-trityl-2H-tetrazol-5-yl)-acetic acid as a solid.

Workup

  1. customat room temperature
  2. filtrationthe precipitate filtered off
  3. dissolutionredissolved in EtOAc (25 ml)
  4. washwashed with saturated aqueous ammonium chloride (2×15 ml)
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. additionwas added
  9. stirringThe resulting mixture was stirred for 18 hrs
  10. customat room temperature
  11. filtrationThe precipitate was filtered off
  12. dissolutiondissolved in water (150 ml)
  13. filtrationThe precipitate was filtered off
  14. washwashed with diethyl ether
  15. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-05975c441f664452ac0030753f29e77e
Source dataset
uspto-grants-2010_04
Patent number
US07700583B2

Reaction notes

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