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Hydrochloric Acid → 7-(2-Methoxyphenyl)-3-(3-((2-methyl-1-naphthyl)oxy)propyl)-1h-indole-2-carboxylic acid

HRID 2199715
ノート
印刷プレビュー

反応式

HRID 2199715 の反応式
O[CH2:2][CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[C:9]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[O:20][CH3:21])[CH:10]=[CH:11][CH:12]=2)[NH:7][C:6]=1[C:22]([O:24]CC)=[O:23].[CH3:27][C:28]1[CH:37]=[CH:36][C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29]=1[OH:38].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O.[Li+].[OH-].Cl>C1COCC1.O.CO>[CH3:21][O:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:8]=1[NH:7][C:6]([C:22]([OH:24])=[O:23])=[C:5]2[CH2:4][CH2:3][CH2:2][O:38][C:29]1[C:30]2[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:36]=[CH:37][C:28]=1[CH3:27]
参加物実験手順後処理出典と根拠反応ノート

参加物

10

反応物 6

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 11776TriphenylphosphineHCID 240552-Methyl-1-naphtholHCID 97268Di-tert-butyl azodicarboxylateHCID 68940496ethyl 3-(3-hydroxypropyl)-7-(2-methoxyphenyl)-1H-indole-2-carboxylate

生成物 1

HCID 25145597
7-(2-Methoxyphenyl)-3-(3-((2-methyl-1-naphthyl)oxy)propyl)-1h-indole-2-carboxylic acid

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a mixture of EXAMPLE 47A (71 mg), 2-methyl-1-naphthol (35 mg), triphenylphosphine (58 mg) in THF (2 mL) and di-tert-butyl azodicarboxylate (55 mg) was stirred at ambient temperature overnight and partitioned between ethyl acetate (150 mL) and water (50 mL). The organic layer was washed with brine and a dried (Na2SO4), filtered and concentrated. The concentrate was purified by flash chromatography on silica gel with 5% ethyl acetate in hexanes to provide an intermediate which was dissolved in THF (2 mL), methanol (1 mL) and water (1 mL) and hydrolyzed with LiOH (100 mg) overnight. The mixture was acidified with 5% HCl and extracted with ethyl acetate. The extract was washed with water and brine and dried (Na2SO4), filtered and concentrated. The concentrate was purified by reverse phase HPLC (C-18, 30 to 100% acetonitrile/water/0.1% TFA). 1H NMR (300 MHz, CDCl3) δ 8.74 (s, 1H), 8.12 (dd, 1H), 7.82 (d, 1H), 7.77 (d, 1H), 7.52 (d, 1H), 7.36-7.47 (m, 5H), 7.27 (d, 1H), 7.09 (t, 2H), 4.10 (t, 2H), 3.83 (s, 3H), 3.48 (t, 2H), 2.46 (s, 3H), 2.38 (m, 2H).

後処理

  1. custompartitioned between ethyl acetate (150 mL) and water (50 mL)
  2. washThe organic layer was washed with brine
  3. dry with materiala dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe concentrate was purified by flash chromatography on silica gel with 5% ethyl acetate in hexanes
  7. customto provide an intermediate which
  8. extractionextracted with ethyl acetate
  9. washThe extract was washed with water and brine
  10. dry with materialdried (Na2SO4)
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customThe concentrate was purified by reverse phase HPLC (C-18, 30 to 100% acetonitrile/water/0.1% TFA)

出典と根拠

ORDレコード
ord-21079d3b32ea41b5880f01dae755380b
出典データセット
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09359296B2

反応ノート

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