N-Iodosuccinimide → HCID 12083025、化合物

HRID 1168500ノート

反応式

HRID 1168500 の反応式
[OH:1][CH2:2][CH:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]1[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13].[I:22]N1C(=O)CCC1=O>CN(C=O)C>[OH:1][CH2:2][CH:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([I:22])[CH:9]=2)[N:4]1[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13]

参加物

4

反応物 2

HCID 120273N-IodosuccinimideHCID 2776402Benzyl 2-(Hydroxymethyl)-1-Indolinecarboxylate

生成物 1

HCID 12083025HCID 12083025、化合物収率 79%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

A solution containing benzyl 2-(hydroxymethyl)-1-indolinecarboxylate (Preparation 6, 1.78 g), N-iodosuccinimide (2.83 g), and anhydrous DMF (12 mL) is stirred overnight at 60° C. in a foil-covered flask. This solution is cooled and concentrated to half volume with a stream of nitrogen. The resulting brown solution is partitioned between water (50 mL) and CH2Cl2 (150 mL). The organic phase is washed with brine, dried (Na2SO4), filtered, and concentrated to give a brown oil. The crude product is chromatographed eluting with 0-40% EtOAc in heptane (300 mL each 10%) to give 2.03 g (79%) of the title compound as a peach solid. Physical characteristics: M.p. 110-111° C.; HRMS (FAB) m/z 410.0270 (C17H16INO3+H). Anal. Found: C, 49.83; H, 3.95; N, 3.37.

後処理

  1. temperatureThis solution is cooled
  2. concentrationconcentrated to half volume with a stream of nitrogen
  3. customThe resulting brown solution is partitioned between water (50 mL) and CH2Cl2 (150 mL)
  4. washThe organic phase is washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a brown oil
  9. customThe crude product is chromatographed
  10. washeluting with 0-40% EtOAc in heptane (300 mL each 10%)

出典と根拠

ORDレコード
ord-6d3878d2ff2d4878bed7de02de17e0d9
出典データセット
uspto-grants-2003_09
特許番号
US06624159B2

反応ノート

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