ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

(S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-((4-nitrophenoxy)-carbonyloxy)ethyl)pyridine 1-oxide → (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-((3-(cyclopropylmethoxy)-4-(methylsulfonamido)-phenylthio)carbonyloxy)ethyl)pyridine 1-oxide

HRID 1776481
ノート
印刷プレビュー

反応式

HRID 1776481 の反応式
[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[C:10]([SH:12])[CH:9]=[CH:8][C:7]=2[NH:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH2:3][CH2:2]1.[Cl:18][C:19]1[CH:20]=[N+:21]([O-:56])[CH:22]=[C:23]([Cl:55])[C:24]=1[CH2:25][C@@H:26]([C:40]1[CH:45]=[CH:44][C:43]([O:46][CH:47]([F:49])[F:48])=[C:42]([O:50][CH2:51][CH:52]2[CH2:54][CH2:53]2)[CH:41]=1)[O:27][C:28](OC1C=CC([N+]([O-])=O)=CC=1)=[O:29]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Cl:55][C:23]1[CH:22]=[N+:21]([O-:56])[CH:20]=[C:19]([Cl:18])[C:24]=1[CH2:25][C@@H:26]([C:40]1[CH:45]=[CH:44][C:43]([O:46][CH:47]([F:49])[F:48])=[C:42]([O:50][CH2:51][CH:52]2[CH2:54][CH2:53]2)[CH:41]=1)[O:27][C:28]([S:12][C:10]1[CH:9]=[CH:8][C:7]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])=[C:6]([O:5][CH2:4][CH:1]2[CH2:2][CH2:3]2)[CH:11]=1)=[O:29]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 86679418(S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-((4-nitrophenoxy)-carbonyloxy)ethyl)pyridine 1-oxideHCID 86679432N-(2-(cyclopropylmethoxy)-4-mercaptophenyl)methanesulfonamide

生成物 1

HCID 71542824(S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-((3-(cyclopropylmethoxy)-4-(methylsulfonamido)-phenylthio)carbonyloxy)ethyl)pyridine 1-oxide

試薬・触媒・溶媒 2

HCID 14284
4-(Dimethylamino)pyridine
触媒
HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of N-(2-(cyclopropylmethoxy)-4-mercaptophenyl)-methanesulfonamide (0.112 g, 0.410 mmol), (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-((4-nitrophenoxy)-carbonyloxy)ethyl)pyridine 1-oxide (prepared with an analogous procedure to that described in Scheme 3, Step 1) (0.200 g, 0.342 mmol), and DMAP (0.021 g, 0.171 mmol) in DCM (8 ml) was stirred at RT overnight. The mixture was diluted with DCM and washed several times with diluted aqueous K2CO3. The organic layer was dried over Na2SO4 and the solvent was removed. The crude was purified by filtration on silica gel cartridge (DCM:EtOAc=80:20) affording the desired compound as a pale yellow amorphous solid. The product was further purified by flash chromatography on silica gel cartridge (petroleum ether:EtOAc=50:50 to 35:65) and by preparative LC/MS affording (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-((3-(cyclopropylmethoxy)-4-(methylsulfonamido)phenylthio)carbonyloxy)ethyl)pyridine 1-oxide as an off-white amorphous solid (0.060 g, 0.083 mmol, 24.40% yield, MS/ESI+ 719.23 [MH]+, [αD]=−64.64, c=0.47 in DCM).

後処理

  1. washwashed several times with diluted aqueous K2CO3
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customthe solvent was removed
  4. filtrationThe crude was purified by filtration on silica gel cartridge (DCM:EtOAc=80:20)

出典と根拠

ORDレコード
ord-f31d73e329ac4591b44318a2ddc6ef6f
出典データセット
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09265768B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート