Potassium Hydroxide → HCID 21245950, compound

HRID 620237Notes

Reaction equation

HRID 620237 reaction equation
[C:1]([C:4]1[CH:27]=[CH:26][C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]2[N:17]=[N:16][C:15]([CH2:18][CH2:19][CH2:20][C:21]([O:23]CC)=[O:22])=[N:14]2)=[C:6]([CH2:28][CH2:29][CH3:30])[C:5]=1[OH:31])(=[O:3])[CH3:2].[OH-].[K+]>C(O)C>[C:1]([C:4]1[CH:27]=[CH:26][C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]2[N:17]=[N:16][C:15]([CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])=[N:14]2)=[C:6]([CH2:28][CH2:29][CH3:30])[C:5]=1[OH:31])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 15614887HCID 15614887, compound

Product 1

HCID 21245950HCID 21245950, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Ethyl 2-[4-(4-acetyl-3-hydroxy-2-(n-propyl) phenoxy)butyl]-2H-tetrazole-5-butanoate (2.4 g) was combined with 5N potassium hydroxide solution (20 ml) in absolute ethanol (20 ml). The mixture was heated to 50° C. for 0.5 hours then cooled to room temperature. The cooled mixture was partitioned between ethyl acetate and water. The organic phase was separated, dried over magnesium sulfate, filtered, and concentrated in vacuo. The concentrate was chromatographed by preparatory-scale HPLC (silica column) eluted with a gradient of 25% to 50% ethyl acetate in hexane plus 1% acetic acid to yield the title product: n.m.r. (300 MHz, CDCl3) δ: 12.80 (s, 1H); 7.54 (d, 1H); 6.35 (d, 1H); 4.60 (t, 2H); 4.01 (t, 2H); 2.82 (m, 2H); 2.57 (t, 2H); 2.51 (s, 3H); 2.20 (m, 4H); 1.95 (m, 2H); 1.80 (m, 2H); 1.46 (m, 2H); 0.88 (t, 3H).

Workup

  1. temperaturethen cooled to room temperature
  2. customThe cooled mixture was partitioned between ethyl acetate and water
  3. customThe organic phase was separated
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe concentrate was chromatographed by preparatory-scale HPLC (silica column)
  8. washeluted with a gradient of 25% to 50% ethyl acetate in hexane plus 1% acetic acid

Sources & evidence

ORD record
ord-97e069641ed84cbd8ada11b49f32aa92
Source dataset
uspto-grants-1989_04
Patent number
US04820723

Reaction notes

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