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Dimethylformamide → (R)-3-(4-(3-methylfuran-2-carboxamido)benzamido)-4-(trimethylammonio)-butanoate

HRID 1958706
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인쇄 미리보기

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HRID 1958706 반응식
[CH3:1][N+:2]([CH2:5][C@H:6]([NH2:11])[CH2:7][C:8]([O-:10])=[O:9])([CH3:4])[CH3:3].[CH3:12][C:13]1[CH:17]=[CH:16][O:15][C:14]=1[C:18]([NH:20][C:21]1[CH:36]=[CH:35][C:24]([C:25](ON2C(=O)CCC2=O)=[O:26])=[CH:23][CH:22]=1)=[O:19].CN(C=O)C.C(N(CC)CC)C>C(OCC)C>[CH3:12][C:13]1[CH:17]=[CH:16][O:15][C:14]=1[C:18]([NH:20][C:21]1[CH:36]=[CH:35][C:24]([C:25]([NH:11][C@@H:6]([CH2:5][N+:2]([CH3:3])([CH3:4])[CH3:1])[CH2:7][C:8]([O-:10])=[O:9])=[O:26])=[CH:23][CH:22]=1)=[O:19]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 121830EmeriamineHCID 866412152,5-Dioxopyrrolidin-1-yl 4-(3-methylfuran-2-carboxamido)benzoate

생성물 1

HCID 59294354(R)-3-(4-(3-methylfuran-2-carboxamido)benzamido)-4-(trimethylammonio)-butanoate수율 43%

시약·촉매·용매 1

HCID 3283
Diethyl Ether
용매

실험 절차

(R)-aminocarnitine (20 mg, 0.12 mmol) and 2,5-dioxopyrrolidin-1-yl 4-(3-methylfuran-2-carboxamido)benzoate (82 mg, 0.24 mmol) were dissolved into DMF (1 mL). Triethylamine (50 μL, 0.36 mmol) was added and the solution was stirred at room temperature for 48 h. Diethyl ether (20 mL) was added and a white precipitate was collected. The powder was purified by silica gel chromatography (elution 10% MeOH/CH2Cl2 to 80% MeOH/CH2Cl2) to give the title compound as a white solid (20 mg, 43%). 1H NMR (400 MHz, D2O) δ 7.62 (d, 1H, J=1.4 Hz), 7.32-7.30 (m, 1H), 7.27-7.16 (m, 3H), 6.55 (d, 1H, J=1.8 Hz), 4.90-4.80 (m, 1H), 3.63-3.42 (m, 2H), 3.13 (s, 9H), 2.48-2.45 (m, 2H), 2.10 (s, 3H); MS ESI 388.2 [M+H]+, calcd for [C20H25N3O5+H]+ 388.18.

후처리

  1. customa white precipitate was collected
  2. customThe powder was purified by silica gel chromatography (elution 10% MeOH/CH2Cl2 to 80% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-00b1304a8e8d445c88a658ea7aeba7c0
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08410150B2

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