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

HRID 1993078노트

반응식

HRID 1993078 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e4680af77fa74ac8ad506c74f984b27f
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07649110B2

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