Tetrahydrofuran → HCID 57652718, compound

HRID 1013269Notes

Reaction equation

HRID 1013269 reaction equation
C[O:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([N:10]2[CH:14]=[N:13][N:12]=[N:11]2)[CH:7]=[C:6]([C:15]2[C:20]([O:21][CH3:22])=[CH:19][CH:18]=[CH:17][N:16]=2)[CH:5]=1.C1COCC1.O[Li].O>CO>[CH3:22][O:21][C:20]1[C:15]([C:6]2[CH:5]=[C:4]([CH:9]=[C:8]([N:10]3[CH:14]=[N:13][N:12]=[N:11]3)[CH:7]=2)[C:3]([OH:23])=[O:2])=[N:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 57652714HCID 57652714, compound

Product 1

HCID 57652718HCID 57652718, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-(3-Methoxy-pyridin-2-yl)-5-tetrazol-1-yl-benzoic acid methyl ester (170 mg, 0.52 mmol) was added to a mixture of THF (20 mL) and MeOH (5 mL) and cooled to ice bath temperature under nitrogen atmosphere. LiOH.H2O (8.8 g, 2.1 mmol) was added, and the reaction mixture was stirred for 18 hours at room temperature. The reaction mixture was concentrated under reduced pressure and 10.0 g of water ice and 10 mL of 10% aqueous HOAc were added to the residue. The resulting mixture was filtered, and the filtrate was washed with 10% aqueous HOAc. The collected solid was dried under vacuum at 60° C. for 3 horus to give 140 mg of 3-(3-methoxy-pyridin-2-yl)-5-tetrazol-1-yl-benzoic acid, MS (M+H)=298.

Workup

  1. temperaturecooled to ice bath temperature under nitrogen atmosphere
  2. concentrationThe reaction mixture was concentrated under reduced pressure and 10.0 g of water ice and 10 mL of 10% aqueous HOAc
  3. additionwere added to the residue
  4. filtrationThe resulting mixture was filtered
  5. washthe filtrate was washed with 10% aqueous HOAc
  6. customThe collected solid was dried under vacuum at 60° C. for 3 horus

Sources & evidence

ORD record
ord-b7f08ca685d241ebb067e409e0d7c947
Source dataset
uspto-grants-2011_07
Patent number
US07981914B2

Reaction notes

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