Ethyl Acetate → HCID 178519232、化合物

HRID 2215091ノート

反応式

HRID 2215091 の反応式
[OH:1][CH:2]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)/[CH:3]=[CH:4]/[C@H:5]1[CH2:9][S:8][C:7](=[O:10])[N:6]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]#[N:18].C([Sn]([N:39]=[N+:40]=[N-:41])(CCCC)CCCC)CCC.C(OCC)(=O)C>C1(C)C=CC=CC=1>[OH:1][CH:2]([CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)/[CH:3]=[CH:4]/[C@H:5]1[CH2:9][S:8][C:7](=[O:10])[N:6]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]1[NH:41][N:40]=[N:39][N:18]=1

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 4984872Tributyltin azideHCID 69601022HCID 69601022、化合物

生成物 1

HCID 178519232HCID 178519232、化合物収率 62.3%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a solution of 4-4 (70 mg, 0.2 mmol) in 0.2 mL toluene was added tributyltin azide (0.27 mL, 1.0 mmol) and the resulting solution was stirred at reflux for 4 hours. Ethyl acetate (100 mL) was added and the solution was quenched with 5% aqueous KF (30 mL) and 1N HCl (30 mL). The layers were separated and the organic layer was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The compound was purified by flash chromatography using 0–5% MeOH/CH2Cl2 to yield 50 mg of 4-5 as a colorless oil. 1H NMR (400 MHz, CD3OD): δ7.29–7.17 (m, 5H), 5.81 (dd, 1H), 5.53 (dd, 1H), 4.38 (q, 1H), 4.33 (q, 1H), 3.45 (dd, 1H), 3.33 (m, 1H), 2.97 (m, 4H), 2.78 (m, 1H), 2.68 (m, 1H), 1.83–1.21 (m, 8H); MS (−ESI): m/z 400.2 (M−1)−.

後処理

  1. temperatureat reflux for 4 hours
  2. customthe solution was quenched with 5% aqueous KF (30 mL) and 1N HCl (30 mL)
  3. customThe layers were separated
  4. washthe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe compound was purified by flash chromatography

出典と根拠

ORDレコード
ord-455b260ecb844ff58982bdd80aa89ac1
出典データセット
uspto-grants-2006_09
特許番号
US07109223B2

反応ノート

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