HCID 69734264、化合物 → HCID 86589157、化合物

HRID 1062900ノート

反応式

HRID 1062900 の反応式
[CH2:1]([N:4]([CH2:25][CH2:26][CH3:27])[C:5]([C:7]1[CH:8]=[C:9]([CH:22]=[CH:23][CH:24]=1)[C:10]([NH:12][C@@H:13]([CH2:18][CH:19]([CH3:21])[CH3:20])[C:14](OC)=[O:15])=[O:11])=[O:6])[CH2:2][CH3:3]>C1(C)C=CC=CC=1>[CH2:25]([N:4]([CH2:1][CH2:2][CH3:3])[C:5]([C:7]1[CH:8]=[C:9]([CH:22]=[CH:23][CH:24]=1)[C:10]([NH:12][C@@H:13]([CH2:18][CH:19]([CH3:21])[CH3:20])[CH:14]=[O:15])=[O:11])=[O:6])[CH2:26][CH3:27]

参加物

3

反応物 1

HCID 69734264HCID 69734264、化合物

生成物 1

HCID 86589157HCID 86589157、化合物収率 52.3%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

実験手順

Methyl(2S)-2-({3-[(dipropylamino)carbonyl]benzoyl}amino)-4-methylpentanoate (1.65 g, 4.4 mmol) in 20 mL of toluene under nitrogen is cooled to −78° C. To this is added, dropwise over 5 min, 11 mL of a 1 M solution of Dibal in toluene. The mixture is stirred an additional 6 minutes, and is then quenched by addition of 2 mL of methanol. The cold bath is removed and 20 mL of a Rochelle salt solution is added and vigorously stirred while the mixture warms to ambient temperature. The product is extracted into ether and the organic phase is washed successively with Rochelle salt solution, water, and brine. It is dried over Na2SO4, concentrated, and chromatographed over silica gel, eluting with 50% ethyl acetate in heptane, to afford the title compound as a colorless oil (0.79 g, 2.3 mmol, 52%). 1H NMR (CDCl3) δ 9.7 (s, 1H), 7.85 (m, 1H), 7.79 (s, 1H), 7.49 (m, 2H), 6.81 (d, J=7 Hz, 1H), 4.78 (m, 1H), 3.46 (br t, 2H), 3.15 (br t, 2H), 1.82 (m, 2H), 1.70 (m, 2H), 1.62-1.53 (m, 3H), 1.01 (m, 9H), 0.75 (br t, 3H).

後処理

  1. additionTo this is added, dropwise over 5 min
  2. customis then quenched by addition of 2 mL of methanol
  3. customThe cold bath is removed
  4. addition20 mL of a Rochelle salt solution is added
  5. stirringvigorously stirred while the mixture
  6. customwarms to ambient temperature
  7. extractionThe product is extracted into ether
  8. washthe organic phase is washed successively with Rochelle salt solution, water, and brine
  9. dry with materialIt is dried over Na2SO4
  10. concentrationconcentrated
  11. customchromatographed over silica gel
  12. washeluting with 50% ethyl acetate in heptane

出典と根拠

ORDレコード
ord-1a3aaafe4bac4fd887f35b6ec8a1cdad
出典データセット
uspto-grants-2005_11
特許番号
US06962934B2

反応ノート

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