Tetrahydrofuran → 2-(3-{(2E)-3-[4-(tert-Butyl)phenyl]prop-2-enoylamino}phenoxy)acetic acid

HRID 2105564Notes

Reaction equation

HRID 2105564 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8](/[CH:11]=[CH:12]/[C:13]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[CH:17]=2)=[O:14])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C1COCC1.Br[CH2:29][C:30]([O:32]C(C)(C)C)=[O:31]>[OH-].[Na+]>[C:1]([C:5]1[CH:6]=[CH:7][C:8](/[CH:11]=[CH:12]/[C:13]([NH:15][C:16]2[CH:17]=[C:18]([CH:19]=[CH:20][CH:21]=2)[O:22][CH2:29][C:30]([OH:32])=[O:31])=[O:14])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 79177tert-Butyl bromoacetateHCID 10214883(2E)-3-[4-(tert-Butyl)phenyl]-N-(3-hydroxyphenyl)prop-2-enamide

Product 1

HCID 101723092-(3-{(2E)-3-[4-(tert-Butyl)phenyl]prop-2-enoylamino}phenoxy)acetic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

To a round-bottomed flask equipped with magnetic stirring was added (2E)-3-[4-(tert-butyl)phenyl]-N-(3-hydroxyphenyl)prop-2-enamide, Example 23, (120 mg, 0.407 mmol), THF (10 mL), tert-butyl bromoacetate (60 uL, 0.407 mmol, Aldrich) and 5 N NaOH (10 mL). The reaction mixture was stirred at 25° C. overnight. The mixture was extracted with EtOAc (20 mL), the organic extract washed with water (20 mL), dried over Na2SO4, filtered and concentrated in vacuo. The resulting residue was treated with trifluoroacetic acid (10 mL), stirred at 25° C. for 2 h, then concentrated in vacuo. Purification by silica gel chromatography (1:2 hexane:EtOAc) provided the title product as an off-white solid. MP 166-172° C. MS (ESI, pos. ion) m/z: 354 (M+1).

Workup

  1. customTo a round-bottomed flask equipped
  2. stirringThe reaction mixture was stirred at 25° C. overnight
  3. extractionThe mixture was extracted with EtOAc (20 mL)
  4. extractionthe organic extract
  5. washwashed with water (20 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. additionThe resulting residue was treated with trifluoroacetic acid (10 mL)
  10. stirringstirred at 25° C. for 2 h
  11. concentrationconcentrated in vacuo
  12. customPurification by silica gel chromatography (1:2 hexane:EtOAc)

Sources & evidence

ORD record
ord-d09cfde221e54bd4bca76479c870a090
Source dataset
uspto-grants-2009_08
Patent number
US07579347B2

Reaction notes

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