N-Iodosuccinimide → HCID 12083025, 화합물

HRID 1168500노트

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HRID 1168500 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

HCID 12083025HCID 12083025, 화합물수율 79%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

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.

후처리

  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%)

출처 및 근거

ORD 기록
ord-6d3878d2ff2d4878bed7de02de17e0d9
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06624159B2

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