Benzoyl chloride → HCID 71077066, 화합물

HRID 2206733노트

반응식

HRID 2206733 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C@H:13]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C@@H:12]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C@H:11]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C@@H:10]([CH2:38][O:39][CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[O:9]2)=[CH:4][C:3]=1[CH2:47][OH:48].[C:49](Cl)(=[O:56])[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1>N1C=CC=CC=1>[C:49]([O:48][CH2:47][C:3]1[CH:4]=[C:5]([C@H:8]2[C@H:13]([O:14][CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[C@@H:12]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C@H:11]([O:30][CH2:31][C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[C@@H:10]([CH2:38][O:39][CH2:40][C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)[O:9]2)[CH:6]=[CH:7][C:2]=1[Cl:1])(=[O:56])[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1

참가 물질

4

반응물 2

HCID 7412Benzoyl chlorideHCID 67288226HCID 67288226, 화합물

생성물 1

HCID 71077066HCID 71077066, 화합물수율 91.7%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

To a solution of alcohol 103 (9.9 g, 14.88 mmol) in pyridine (36 mL) was added benzoyl chloride (1.9 mL, 16.37 mmol) at room temperature. The mixture was stirred at room temperature for 6 hours. The mixture was washed with aq. saturated NaHCO3 solution. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography to provide the mixture of anomers of the title compound (10.5 g). The anomeric mixture of 104 was recrystallized with IPA (150 mL). The precipitate was collected by filtration and washed with cold IPA (50 mL) and dried under high vacuum to obtain β-anomer of the title compound 104 (6.13 g, 54%).

후처리

  1. washThe mixture was washed with aq. saturated NaHCO3 solution
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography
  6. customto provide

출처 및 근거

ORD 기록
ord-eb8c6fd3ca774595849333584f949910
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09371303B2

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