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醋酸 → 3,5-dichloro-4-((S)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-((S)-3-(3-((phenylamino)methyl)benzoyl)thiazolidine-2-carbonyloxy)ethyl)pyridine 1-oxide

HRID 1754312
笔记
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反应方程式

HRID 1754312 反应方程式
[Cl:1][C:2]1[CH:3]=[N+:4]([O-:44])[CH:5]=[C:6]([Cl:43])[C:7]=1[CH2:8][C@@H:9]([C:28]1[CH:33]=[CH:32][C:31]([O:34][CH:35]([F:37])[F:36])=[C:30]([O:38][CH2:39][CH:40]2[CH2:42][CH2:41]2)[CH:29]=1)[O:10][C:11]([C@H:13]1[N:17]([C:18](=[O:27])[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH:25]=O)[CH:20]=2)[CH2:16][CH2:15][S:14]1)=[O:12].[NH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[N+:4]([O-:44])[CH:5]=[C:6]([Cl:43])[C:7]=1[CH2:8][C@@H:9]([C:28]1[CH:33]=[CH:32][C:31]([O:34][CH:35]([F:37])[F:36])=[C:30]([O:38][CH2:39][CH:40]2[CH2:42][CH2:41]2)[CH:29]=1)[O:10][C:11]([C@H:13]1[N:17]([C:18](=[O:27])[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][NH:45][C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[CH:20]=2)[CH2:16][CH2:15][S:14]1)=[O:12]
参与物实验过程后处理来源与证据反应笔记

参与物

6

反应物 4

HCID 176醋酸HCID 6115苯胺-1-13CHCID 5049666三乙酰氧基硼氢化钠HCID 867202713,5-dichloro-4-((S)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-((S)-3-(3-formylbenzoyl)thiazolidine-2-carbonyloxy)ethyl)pyridine 1-oxide

产物 1

HCID 867202723,5-dichloro-4-((S)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-((S)-3-(3-((phenylamino)methyl)benzoyl)thiazolidine-2-carbonyloxy)ethyl)pyridine 1-oxide
收率 100%

试剂、催化剂与溶剂 1

HCID 6344二氯甲烷溶剂2 次

实验过程

3,5-dichloro-4-((S)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-((S)-3-(3-formylbenzoyl)thiazolidine-2-carbonyloxy)ethyl)pyridine 1-oxide (108 mg, 0.162 mmol) was dissolved in DCM (2 ml). Aniline (18.08 mg, 0.194 mmol) and acetic acid (9.26 μL, 0.162 mmol) were added, and the mixture was stirred at RT for 1 hour. Sodium triacetoxyborohydride (51.4 mg, 0.243 mmol) was added, and the mixture was stirred at RT overnight to achieve completion. The reaction mixture was diluted with DCM and extracted with water (2×). The organic phase was dried over Na2SO4 and concentrated under vacuum to give 3,5-dichloro-4-((S)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-((S)-3-(3-((phenylamino)methyl)benzoyl)thiazolidine-2-carbonyloxy)ethyl)pyridine 1-oxide (120 mg, 0.161 mmol, 100% yield). The compound was used in the next step without any further purification.

后处理

  1. stirringthe mixture was stirred at RT overnight
  2. extractionextracted with water (2×)
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated under vacuum

来源与证据

ORD记录
ord-1ac78abc219341b39b1a0c8f6142f2d5
来源数据集
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
专利号
US09169245B2

反应笔记

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本页导航参与物实验过程后处理来源与证据反应笔记