Lithium Hydroxide → HCID 16228176, compound

HRID 1809160Notes

Reaction equation

HRID 1809160 reaction equation
C[O:2][C:3](=[O:18])[CH:4]([O:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N:13]2[CH:17]=[N:16][N:15]=[N:14]2)[CH:8]=1)[CH3:5].[Li+].[OH-].O1CCOCC1>>[N:13]1([C:9]2[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=2)[O:6][CH:4]([CH3:5])[C:3]([OH:18])=[O:2])[CH:17]=[N:16][N:15]=[N:14]1

Participants

4

Reactant 3

HCID 3939Lithium HydroxideHCID 312751,4-DioxaneHCID 59708657HCID 59708657, compound

Product 1

HCID 16228176HCID 16228176, compoundYield 98%

Procedure

To a 25 mL round-bottom flask equipped with a magnetic stir bar was added 2-(3-tetrazol-1-yl-phenoxy)-propionic acid methyl ester 30 (326 mg, 1.3 mmol, 1.0 eq.), 2N LiOH (2.6 mL, 2.6 mmol, 2.0 eq), and 1,4-dioxane (2.6 ml, 2.6 mmol, 2.0 eq). The reaction mixture was then stirred at room temperature for 3 hours. The reaction mixture was concentrated, diluted with water (5 mL), acidified with 1 N HCl (adjust pH=3.5), and then extracted with 3× EtOAc (25 mL each). The organic layer was dried with Na2SO4, concentrated, and dried under high vacuum to yield 2-(3-tetrazol-1-yl-phenoxy)-propionic acid 31 (230.3 mg, 98% yield). LC/MSD (HP Series 1100 MSD) MS (ES+) m/z 235.0 (M+H)+1 1H-NMR, Varian 400 MHz (MeOH-d4) δ 9.76 (s, 1H), 7.52 (t, 1H), 7.45 (d, 2H), 7.08 (d, 1H), 4.93 (q, 1H), 1.62 (d, 3H) ppm.

Workup

  1. customTo a 25 mL round-bottom flask equipped with a magnetic stir bar
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with water (5 mL)
  4. extractionextracted with 3× EtOAc (25 mL each)
  5. dry with materialThe organic layer was dried with Na2SO4
  6. concentrationconcentrated
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-8f1357158ab34244ab0096e4808f86ad
Source dataset
uspto-grants-2013_01
Patent number
US08362017B2

Reaction notes

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