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

HRID 349293노트

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HRID 349293 반응식
CS(C)=O.[CH3:5][O:6][C:7](=[O:23])[CH2:8][CH2:9][CH2:10][C:11]#[C:12][CH2:13][N:14]1[C:19](=[O:20])[CH2:18][CH2:17][CH2:16][CH:15]1[CH2:21][OH:22].FC(F)(F)C([O-])=O.[NH+]1C=CC=CC=1>C1C=CC=CC=1>[CH3:5][O:6][C:7](=[O:23])[CH2:8][CH2:9][CH2:10][C:11]#[C:12][CH2:13][N:14]1[C:19](=[O:20])[CH2:18][CH2:17][CH2:16][CH:15]1[CH:21]=[O:22]

참가 물질

5

반응물 3

HCID 679Dimethyl SulfoxideHCID 9813011pyridine TFAHCID 690203407-(2-Hydroxymethyl-6-oxo-piperidin-1-yl)-hept-5-ynoic acid methyl ester

생성물 1

HCID 860125007-(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

1-(3-(Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI, 530 mg, 2.76 mmol) and DMSO (0.26 mL, 3.68 mmol) were added sequentially to a solution of 7-(2-hydroxymethyl-6-oxo-piperidin-1-yl)-hept-5-ynoic acid methyl ester (246 mg, 0.92 mmol) in benzene (7.0 mL) at rt. The mixture was cooled to 0° C. and pyridinium trifluoroacetate (196 mg, 1.01 mmol) was added. The reaction was allowed to warm to rt and then was stirred at rt for 2.5 h. The solution was decanted from the oily residue and the residue was washed with benzene (3×5 mL). The combined benzene phases were concentrated in vacuo to afford crude 7-(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 (3×5 mL)
  4. concentrationThe combined benzene phases were concentrated in vacuo

출처 및 근거

ORD 기록
ord-5b34f265fd4543b1879cc269ea10dbe1
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07179820B2

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