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

HRID 1160329ノート

反応式

HRID 1160329 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-41ce9f2f3f01423ba29e47b58fdf4302
出典データセット
uspto-grants-2010_10
特許番号
US07816367B2

反応ノート

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