tert-Butanol → HCID 90132491、化合物

HRID 2275787ノート

反応式

HRID 2275787 の反応式
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH:12]([C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)[CH2:13]C(O)=O.C(N(CC)CC)C.[N:31]12[CH2:38]CN(CC1)CC2.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:46])C=CC=CC=1.[C:56]([OH:60])([CH3:59])([CH3:58])[CH3:57]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH:12]([C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)[CH2:13][NH:31][C:38](=[O:46])[O:60][C:56]([CH3:59])([CH3:58])[CH3:57]

参加物

8

反応物 5

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 9237DabcoHCID 199401P,P-Diphenylphosphinic azideHCID 3816170HCID 3816170、化合物

生成物 1

HCID 90132491HCID 90132491、化合物

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Under argon, a solution of 3.2 g of rac-3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-(4-fluorophenyl)propanoic acid (Example 47A, 8.78 mmol) in 32 ml of toluene was initially charged, and 1.33 g of triethylamine (13.18 mmol), 98 mg of 1,4-diazabicyclo[2.2.2]octane (0.88 mmol), 3.14 g of diphenylphosphoryl azide (11.42 mmol) and 6.51 g of tert-butanol (87.84 mmol) were added. The reaction mixture was heated at reflux overnight and then diluted with ethyl acetate and washed with water. The organic phase was dried over sodium sulphate, filtered and concentrated. The crude product was purified by silica gel chromatography (mobile phase: cyclohexane/ethyl acetate 8:1; 6:1). This gave 959 mg of the title compound (28% of theory).

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. washwashed with water
  4. dry with materialThe organic phase was dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by silica gel chromatography (mobile phase: cyclohexane/ethyl acetate 8:1; 6:1)

出典と根拠

ORDレコード
ord-bebad59cf44442a883d375d9d7e67674
出典データセット
uspto-grants-2015_09
特許番号
US09126998B2

反応ノート

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