Sodium hydride → Diethyl (S)-1-(1-((tert-butoxycarbonyl)amino)propan-2-yl)-1H-pyrrolo[2,3-b]pyridine-2,6-dicarboxylate

HRID 1521723노트

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HRID 1521723 반응식
[H-].[Na+].[NH:3]1[C:7]2=[N:8][C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][CH:11]=[C:6]2[CH:5]=[C:4]1[C:17]([O:19][CH2:20][CH3:21])=[O:18].[CH3:22][C@@H:23]1OS(=O)(=O)[N:25]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:24]1>CN(C=O)C>[C:33]([O:32][C:30]([NH:25][CH2:24][C@@H:23]([N:3]1[C:7]2=[N:8][C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][CH:11]=[C:6]2[CH:5]=[C:4]1[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH3:22])=[O:31])([CH3:36])([CH3:35])[CH3:34]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 11195739(s)-Tert-butyl 5-methyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxideHCID 67236396Diethyl 1H-pyrrolo[2,3-B]pyridine-2,6-dicarboxylate2회

생성물 1

HCID 67238103Diethyl (S)-1-(1-((tert-butoxycarbonyl)amino)propan-2-yl)-1H-pyrrolo[2,3-b]pyridine-2,6-dicarboxylate수율 63%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

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온도
0 °C

실험 절차

To a suspension of 60% sodium hydride in mineral oil (503 mg, 12.6 mmol) in DMF (10 mL) cooled to 0° C. is added a solution of diethyl 1H-pyrrolo[2,3-b]pyridine-2,6-dicarboxylate (Intermediate D, 3.00 g, 11.4 mmol) in DMF (10 mL), dropwise. The mixture is stirred at 0° C. for 30 min after which a solution of tert-butyl (5S)-5-methyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide (2.71 g, 11.4 mmol) in DMF (10 mL) is added. The mixture is allowed to warm and stir at room temperature for 16 h. The reaction is quenched with H2O and is stirred for 15 min. The mixture is extracted with ethyl acetate and the combined organic phases are washed with brine and are dried (Na2SO4). The solvent is removed in vacuo and the crude material is purified via flash column chromatography using a gradient elution of 0-30% ethyl acetate/heptane to afford the title compound (3.00 g, 63%). LCMS: 442.86 (M+Na+).

후처리

  1. additionis added
  2. temperatureto warm
  3. customThe reaction is quenched with H2O
  4. stirringis stirred for 15 min
  5. extractionThe mixture is extracted with ethyl acetate
  6. washthe combined organic phases are washed with brine
  7. dry with materialare dried (Na2SO4)
  8. customThe solvent is removed in vacuo
  9. customthe crude material is purified via flash column chromatography
  10. washa gradient elution of 0-30% ethyl acetate/heptane

출처 및 근거

ORD 기록
ord-9707583393d34f6fa38b2af6aea0d0ff
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073926B2

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