Methyl 4-fluorobenzoylacetate → HCID 86658322, 화합물

HRID 1890270노트

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HRID 1890270 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.[Cl-].[CH3:16][CH:17]1[CH2:21][CH2:20][C:19](=[O:22])[N:18]1[NH3+:23]>N1C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[N:23][N:18]2[C:19](=[O:22])[CH2:20][CH2:21][CH:17]2[CH3:16])[CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 579425Methyl 4-fluorobenzoylacetateHCID 67437276HCID 67437276, 화합물

생성물 1

HCID 86658322HCID 86658322, 화합물수율 93.1%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

A mixture of 7.50 g (38.2 mmol) of methyl 3-(4-fluorophenyl)-3-oxopropanoate and 11.5 g (76.5 mmol) of 2-methyl-5-oxopyrrolidin-1-aminium chloride in 50 ml of pyridine is stirred at room temperature for 72 h. The reaction mixture is concentrated under reduced pressure. Purification by column chromatography on silica gel (cyclohexane/ethyl acetate) gives 10.4 g (93%) of the desired product as a mixture of isomers; log P(HCOOH): 2.13 and 2.45; 1H-NMR (ppm): δ (DMSO-d6)=1.16-1.19 (m, 3H), 1.58-1.62 (m, 2H), 2.20-2.22 (m, 1H), 2.36-2.41 (m, 1H), 3.54 (s, 2.25H), 3.64 (s, 0.75H), 3.80 (d, 1H), 3.90 (d, 1H), 3.80 (q, 1H), 7.24 (t, 0.6H), 7.29 (t, 1.4H), 7.44-7.47 (m, 0.6H), 7.89-7.92 (m, 1.4H); LC-MS: m/z=293 [M+H]+.

후처리

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. customPurification by column chromatography on silica gel (cyclohexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-8588c0f702404ffb8dedc474e606fe99
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08507472B2

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