Tetrahydrofuran → {[6-(1,5-diphenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}acetic acid

HRID 456842노트

반응식

HRID 456842 반응식
[C:1]1([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:10][CH:9]=[C:8]2[C:18]2[CH:19]=[C:20]3[C:25](=[CH:26][CH:27]=2)[CH:24]=[C:23]([O:28][CH2:29][C:30]([O:32]C)=[O:31])[CH:22]=[CH:21]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[C@H](NCCC1C=CC(O)=CC=1)[C@H](O)C1C=CC(O)=CC=1.[OH-].[Na+].C1COCC1>O.CO>[C:1]1([N:7]2[C:11]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[CH:10][CH:9]=[C:8]2[C:18]2[CH:19]=[C:20]3[C:25](=[CH:26][CH:27]=2)[CH:24]=[C:23]([O:28][CH2:29][C:30]([OH:32])=[O:31])[CH:22]=[CH:21]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 33572RitodrineHCID 86603528methyl {[6-(1,5-diphenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}acetate

생성물 1

HCID 11618606{[6-(1,5-diphenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}acetic acid수율 90.5%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

반응 조건

온도
65 °C

실험 절차

In a similar manner as described in step 2 of Example 6, the title compound was prepared from methyl {[6-(1,5-diphenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}acetate (0.17 g, 0.39 mmol), prepar in the previous step, and 1N NaOH (0.59 mL, 0.59 mmol) in 5:5:1 THF:MeOH:water (55 mL) with the exception that this reaction required heating to 65° C. and was complete after 6 hours. The still warm reaction mixture was filtered and then allowed to cool to ambient temperature. The mixture was acidified with 1N HCl (2.5 mL) and the volatiles were removed under reduced pressure (without the addition of heat). The resulting slurry was diluted with water (25 mL) and the solids were isolated by filtration to give {[6-(1,5-diphenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}acetic acid as an off-white solid (0.148 g, 90%), mp 258–260° C. (dec). Elemental Analysis for C28H21NO3.0.23 H2O Calc'd: C, 79.39; H, 5.11; N, 3.31. Found: C, 78.84; H 5.03; N, 3.00.

후처리

  1. customThe still warm reaction mixture
  2. filtrationwas filtered
  3. temperatureto cool to ambient temperature
  4. customthe volatiles were removed under reduced pressure (
  5. additionwithout the addition
  6. temperatureof heat)
  7. additionThe resulting slurry was diluted with water (25 mL)
  8. customthe solids were isolated by filtration

출처 및 근거

ORD 기록
ord-d5a9add9b5fe4aaeba2b838b3950ea22
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07186749B2

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