2,5-Dimethoxytetrahydrofuran → 3-(4-Hydroxyphenyl)-3-(1H-pyrrol-1-yl)propanoic acid

HRID 1160329Notes

Reaction equation

HRID 1160329 reaction equation
CO[CH:3]1[CH2:7][CH2:6][CH:5](OC)O1.[NH2:10][CH:11]([C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)[CH2:12][C:13]([OH:15])=[O:14].C([O-])(=O)C.[Na+]>C(O)(=O)C>[OH:22][C:19]1[CH:18]=[CH:17][C:16]([CH:11]([N:10]2[CH:3]=[CH:7][CH:6]=[CH:5]2)[CH2:12][C:13]([OH:15])=[O:14])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 790982,5-DimethoxytetrahydrofuranHCID 4403113-Amino-3-(4-hydroxyphenyl)propanoic acidHCID 517045Sodium Acetate

Product 1

HCID 591327223-(4-Hydroxyphenyl)-3-(1H-pyrrol-1-yl)propanoic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

At 100° C., 2,5-dimethoxytetrahydrofuran (8.5 mmol) was added to a mixture of 3-amino-3-(4-hydroxyphenyl) propanoic acid (7.7 mmol) and sodium acetate (46 mmol) in acetic acid (34 mL). After stirring for 1 h, acetic acid was removed under reduced pressure. The residue was extracted with ethyl acetate (300 mL). The organic layer was washed with brine and dried over anhydrous Na2SO4 and concentrated. The residue was purified via column chromatography (10% methanol in dichloromethane) to compound 55.1. LC-MS (neg.) m/e: 230.2 (M−H).

Workup

  1. customacetic acid was removed under reduced pressure
  2. extractionThe residue was extracted with ethyl acetate (300 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified via column chromatography (10% methanol in dichloromethane) to compound 55.1

Sources & evidence

ORD record
ord-41ce9f2f3f01423ba29e47b58fdf4302
Source dataset
uspto-grants-2010_10
Patent number
US07816367B2

Reaction notes

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