3-Hydroxyazetidine hydrochloride → 1-[3-Chloro-6-[2-(3-hydroxy-azetidin-1-yl)-ethoxy]-4-methoxy-2-methyl-5-(3-phenyl-propoxy)-phenyl]-ethanone

HRID 219476

반응식

HRID 219476 반응식
Br[CH2:2][CH2:3][O:4][C:5]1[C:10]([O:11][CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:9]([O:21][CH3:22])[C:8]([Cl:23])=[C:7]([CH3:24])[C:6]=1[C:25](=[O:27])[CH3:26].Cl.[OH:29][CH:30]1[CH2:33][NH:32][CH2:31]1>>[Cl:23][C:8]1[C:7]([CH3:24])=[C:6]([C:25](=[O:27])[CH3:26])[C:5]([O:4][CH2:3][CH2:2][N:32]2[CH2:33][CH:30]([OH:29])[CH2:31]2)=[C:10]([O:11][CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]=1[O:21][CH3:22]

참가 물질

3

반응물 2

HCID 27592903-Hydroxyazetidine hydrochlorideHCID 595834951-[2-(2-Bromo-ethoxy)-5-chloro-4-methoxy-6-methyl-3-(3-phenyl-propoxy)-phenyl]-ethanone

생성물 1

HCID 252543731-[3-Chloro-6-[2-(3-hydroxy-azetidin-1-yl)-ethoxy]-4-methoxy-2-methyl-5-(3-phenyl-propoxy)-phenyl]-ethanone수율 16%

실험 절차

Example 34b (207 mg, 0.46 mmol), CsCO3 (2.48 eq.) and 3-hydroxyazetidine hydrochloride (1.4 eq.) were reacted as described under General Procedure L and the crude product was purified by flash chromatography (silica gel, hexane/Et2O 1:1) to afford the title compound as a pale yellow oil (34 mg, 16%). 1H NMR (300 MHz, CDCl3) δ 7.33-7.20 (m, 5H), 4.40 (quintet, J=5.7 Hz, 1H), 4.07 (t, J=6.5 Hz, 2H), 3.98 (t, J=5.7 Hz, 2H), 3.88 (s, 3H), 3.67-3.62 (m, 2H), 2.96-2.91 (m, 2H), 2.85-2.80 (m, 2H), 2.73 (t, J=5.7 Hz, 2H), 2.51 (s, 3H), 2.19 (s, 3H), 2.13-2.03 (m, 2H). MS (ES+) m/z 448.2 (M+H+).

후처리

  1. customthe crude product was purified by flash chromatography (silica gel, hexane/Et2O 1:1)

출처 및 근거

ORD 기록
ord-ea511563eaac4a8eb94add805345610e
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202513B2

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