Dimethyl Sulfoxide → 7-((R)-2-formyl-6-oxo-piperidin-1-yl)-heptanoic acid methyl ester

HRID 349312노트

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HRID 349312 반응식
CCN=C=NCCCN(C)C.CS(C)=O.[CH3:16][O:17][C:18](=[O:34])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][N:25]1[C:30](=[O:31])[CH2:29][CH2:28][CH2:27][C@@H:26]1[CH2:32][OH:33].FC(F)(F)C([O-])=O.[NH+]1C=CC=CC=1>C1C=CC=CC=1>[CH3:16][O:17][C:18](=[O:34])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][N:25]1[C:30](=[O:31])[CH2:29][CH2:28][CH2:27][C@@H:26]1[CH:32]=[O:33]

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 9813011pyridine TFAHCID 690230257-((R)-2-hydroxymethyl-6-oxo-piperidin-1-yl)-heptanoic acid methyl ester

생성물 1

HCID 865952947-((R)-2-formyl-6-oxo-piperidin-1-yl)-heptanoic acid methyl ester

시약·촉매·용매 1

HCID 241Benzene용매

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온도
0 °C

실험 절차

EDCI (119 mg, 0.62 mmol) and DMSO (59 μL, 0.83 mmol) were added sequentially to a solution of 7-((R)-2-hydroxymethyl-6-oxo-piperidin-1-yl)-heptanoic acid methyl ester (56 mg, 0.21 mmol) in benzene (2.0 mL) at rt. The mixture was cooled to 0° C. and pyridinium trifluoroacetate (44 mg, 0.23 mmol) was added. The reaction was allowed to warm to rt and then was stirred at rt for 3 h. The solution was decanted from the oily residue and the residue was washed with benzene (3×2 mL). The combined benzene phases were concentrated in vacuo to afford crude 7-((R)-2-formyl-6-oxo-piperidin-1-yl)-heptanoic acid methyl ester that was used without further purification.

후처리

  1. temperatureto warm to rt
  2. customThe solution was decanted from the oily residue
  3. washthe residue was washed with benzene (3×2 mL)
  4. concentrationThe combined benzene phases were concentrated in vacuo

출처 및 근거

ORD 기록
ord-3d07f8088dae426cb53d121eb8ea217e
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07179820B2

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