Dimethyl Sulfoxide → 7-((R)-2-formyl-6-oxo-piperidin-1-yl)-hept-5-ynoic acid methyl ester

HRID 349319노트

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HRID 349319 반응식
CCN=C=NCCCN(C)C.CS(C)=O.[CH3:16][O:17][C:18](=[O:34])[CH2:19][CH2:20][CH2:21][C:22]#[C: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][C:22]#[C: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 690212337-((R)-2-hydroxymethyl-6-oxo-piperidin-1-yl)-hept-5-ynoic acid methyl ester

생성물 1

HCID 865952957-((R)-2-formyl-6-oxo-piperidin-1-yl)-hept-5-ynoic acid methyl ester

시약·촉매·용매 1

HCID 241Benzene용매

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온도
0 °C

실험 절차

EDCI (127 mg, 0.66 mmol) and DMSO (62 μL, 0.87 mmol) were added sequentially to a solution of 7-((R)-2-hydroxymethyl-6-oxo-piperidin-1-yl)-hept-5-ynoic acid methyl ester (prepared in accordance with Example 29, step 3, 59 mg, 0.22 mmol) in benzene (2.0 mL) at rt. The mixture was cooled to 0° C. and pyridinium trifluoroacetate (47 mg, 0.24 mmol) was added. The reaction was allowed to warm to rt and then was stirred at rt for 2 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)-hept-5-ynoic 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-e667844fc12e40eeb88c918d076b444e
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07179820B2

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