Dimethylamine → 2-(Dimethylamino)ethyl 5-(tetradecyloxy)furan-2-carboxylate

HRID 335537

반응식

HRID 335537 반응식
[CH2:1]([O:15][C:16]1[O:20][C:19]([C:21]([O:23][CH2:24][CH2:25]Br)=[O:22])=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[CH3:27][NH:28][CH3:29]>C1COCC1>[CH2:1]([O:15][C:16]1[O:20][C:19]([C:21]([O:23][CH2:24][CH2:25][N:28]([CH3:29])[CH3:27])=[O:22])=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

참가 물질

4

반응물 2

HCID 674DimethylamineHCID 498698992-Bromoethyl 5-(tetradecyloxy)furan-2-carboxylate

생성물 1

HCID 498701652-(Dimethylamino)ethyl 5-(tetradecyloxy)furan-2-carboxylate수율 71%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of 2-bromoethyl 5-(tetradecyloxy)furan-2-carboxylate (0.186 g, 0.43 mmol) (prepared in Example 5) in THF at 0° C. was added dimethylamine (1 mL of a 2M solution in THF, 2.15 mmol) with stirring. The solution was allowed to warm to room temperature and stirring was continued for 12 hrs at which time the reaction was concentrated to dryness. The crude material was purified by flash chromatography eluting with ethyl acetate in hexanes (5-35%) to yield 0.121 g (71%) of the title compound as a waxy, colourless solid. MS (m/z, ES+): 396.29 (M+1, 100%); 1H NMR (400 MHz, DMSO-d6) δ: 7.2 (d, 1H), 5.6 (d, 1H), 4.23 (t, 2H), 4.13 (t, 2H), 2.53 (t, 2H), 2.18 (s, 6H), 1.7 (p, 2H), 1.2-1.5 (m, 22H), 0.85 (t, 3H).

후처리

  1. stirringstirring
  2. concentrationthe reaction was concentrated to dryness
  3. customThe crude material was purified by flash chromatography
  4. washeluting with ethyl acetate in hexanes (5-35%)

출처 및 근거

ORD 기록
ord-887bb610d8174f36a0850033d1a95458
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08884034B2

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