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

HRID 1776474
ノート
印刷プレビュー

反応式

HRID 1776474 の反応式
[SH:1][C:2]1[CH:3]=[C:4]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.[Cl:13][C:14]1[CH:15]=[N+:16]([O-:51])[CH:17]=[C:18]([Cl:50])[C:19]=1[CH2:20][C@@H:21]([C:35]1[CH:40]=[CH:39][C:38]([O:41][CH:42]([F:44])[F:43])=[C:37]([O:45][CH2:46][CH:47]2[CH2:49][CH2:48]2)[CH:36]=1)[O:22][C:23](OC1C=CC([N+]([O-])=O)=CC=1)=[O:24]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:50][C:18]1[CH:17]=[N+:16]([O-:51])[CH:15]=[C:14]([Cl:13])[C:19]=1[CH2:20][C@@H:21]([C:35]1[CH:40]=[CH:39][C:38]([O:41][CH:42]([F:44])[F:43])=[C:37]([O:45][CH2:46][CH:47]2[CH2:49][CH2:48]2)[CH:36]=1)[O:22][C:23]([S:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH:8][S:9]([CH3:12])(=[O:10])=[O:11])[CH:3]=1)=[O:24]
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 57180113N-(3-mercaptophenyl)methanesulfonamideHCID 86679418(S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-((4-nitrophenoxy)-carbonyloxy)ethyl)pyridine 1-oxide

生成物 1

HCID 71542652(S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-((3-(methylsulfonamido) phenylthio)carbonyloxy)ethyl)pyridine 1-oxide収率 73.4%

試薬・触媒・溶媒 2

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

実験手順

To a suspension of N-(3-mercaptophenyl)methanesulfonamide (97 mg, 0.478 mmol) in DCM (15 ml), under nitrogen atmosphere, (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) (200 mg, 0.342 mmol), and DMAP (20.87 mg, 0.171 mmol) were added, and the reaction mixture was stirred at RT for 3 hours. The organic solution was washed with K2CO3 dil. aq., dried over Na2SO4, filtered and evaporated. The crude was triturated with EtOH affording (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-((3-(methylsulfonamido) phenylthio)carbonyloxy)ethyl)pyridine 1-oxide (162.9 mg, 0.251 mmol, 73.4% yield, MS/ESI+ 649.04 [MH]+, [αD]=−93.81, c=0.53 in DCM).

後処理

  1. additionwere added
  2. washThe organic solution was washed with K2CO3 dil. aq.
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude was triturated with EtOH

出典と根拠

ORDレコード
ord-702ec6fb47304a4498ffc71c322a37b9
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

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