Hydrochloric Acid → HCID 57889538, compound

HRID 1016182Notes

Reaction equation

HRID 1016182 reaction equation
[CH2:1]([O:8][CH2:9][N:10]1[N:14]=[N:13][C:12]([C:15]2[CH:16]=[C:17]([CH:23]=[CH:24][CH:25]=2)[C:18]([O:20]CC)=[O:19])=[N:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Li+].Cl>C1COCC1>[CH2:1]([O:8][CH2:9][N:10]1[N:14]=[N:13][C:12]([C:15]2[CH:16]=[C:17]([CH:23]=[CH:24][CH:25]=2)[C:18]([OH:20])=[O:19])=[N:11]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium Hydroxide2×HCID 57888757Ethyl 3-(2-(benzyloxymethyl)-2H-tetrazol-5-yl)benzoate

Product 1

HCID 57889538HCID 57889538, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 3-(2-(benzyloxymethyl)-2H-tetrazol-5-yl)benzoate (653 mg, 1.93 mmol) in THF (10 mL) was treated with a 0.5 M aqueous lithium hydroxide solution (5.8 mL, 2.9 mmol), and the reaction was stirred overnight. Analysis by LC/MS indicated that the reaction had not gone to completion, so the mixture was treated with a 0.5 M aqueous lithium hydroxide solution (1 mL, 0.5 mmol), and the reaction was stirred for an additional 6 hours. The THF was removed under reduced pressure, and the aqueous solution was treated with 1 N HCl (3.5 mL, 3.5 mmol). The mixture was extracted 3× with ethyl acetate, and the combined organic phases were dried over sodium sulfate and concentrated in-vacuo to yield the title compound as a colorless powder which was used as-is in the next step.

Workup

  1. stirringthe reaction was stirred for an additional 6 hours
  2. customThe THF was removed under reduced pressure
  3. extractionThe mixture was extracted 3× with ethyl acetate
  4. dry with materialthe combined organic phases were dried over sodium sulfate
  5. concentrationconcentrated in-vacuo

Sources & evidence

ORD record
ord-f638197cb22e401585c13c98a72b4050
Source dataset
uspto-grants-2011_07
Patent number
US07985861B2

Reaction notes

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