Triethylamine → 5-[3-chloro-4-(methylsulfonyl)phenyl]-1-[5-(1,3-dioxolan-2-yl)pyridin-2-yl]-6-[(2R,3R,7R)-2,3-diphenyl-1,4-dioxaspiro[4.4]non-7-yl]hexane-1,4-dione

HRID 1881914노트

반응식

HRID 1881914 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]([CH2:17][C@H:18]2[CH2:38][CH2:37][C:20]3([O:24][C@H:23]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[C@@H:22]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[O:21]3)[CH2:19]2)[C:13](=[O:16])[CH:14]=[CH2:15])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].[O:39]1[CH2:43][CH2:42][O:41][CH:40]1[C:44]1[CH:45]=[CH:46][C:47]([CH:50]=[O:51])=[N:48][CH:49]=1.C(N(CC)CC)C>C(O)C.[Cl-].C([N+]1C(C)=C(CCO)SC=1)C1C=CC=CC=1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]([CH2:17][C@H:18]2[CH2:38][CH2:37][C:20]3([O:21][C@H:22]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[C@@H:23]([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)[O:24]3)[CH2:19]2)[C:13](=[O:16])[CH2:14][CH2:15][C:50]([C:47]2[CH:46]=[CH:45][C:44]([CH:40]3[O:41][CH2:42][CH2:43][O:39]3)=[CH:49][N:48]=2)=[O:51])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:9])=[O:10]

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 592551735-(1,3-Dioxolan-2-yl)picolinaldehydeHCID 59331594HCID 59331594, 화합물

생성물 1

HCID 593312385-[3-chloro-4-(methylsulfonyl)phenyl]-1-[5-(1,3-dioxolan-2-yl)pyridin-2-yl]-6-[(2R,3R,7R)-2,3-diphenyl-1,4-dioxaspiro[4.4]non-7-yl]hexane-1,4-dione수율 33.4%

시약·촉매·용매 3

HCID 28333523-Benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chloride촉매HCID 702Ethanol용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 4-[3-chloro-4-(methylsulfonyl)phenyl]-5-[(2R,3R,7R)-2,3-diphenyl-1,4-dioxaspiro[4.4]non-7-yl]pent-1-en-3-one (624 mg) in ethanol (5 mL) were added 5-(1,3-dioxolan-2-yl)pyridine-2-carbaldehyde (244 mg), 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride (33.7 mg) and triethylamine (68 μL), and the mixture was stirred with heating under reflux for 1 hr. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate and washed with water. The ethyl acetate layer was dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (276 mg, yield 33%) was obtained as a pale-yellow amorphous solid from a fraction eluted with ethyl acetate-hexane (2:1, volume ratio).

후처리

  1. temperaturewith heating
  2. temperatureunder reflux for 1 hr
  3. washwashed with water
  4. dry with materialThe ethyl acetate layer was dried (MgSO4)
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-7c94c81349d140b7b7dd81e0ebf60874
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08318746B2

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