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

Diisopropylethylamine → 5-[4-(3,5-di-tert-butyl-4-hydroxy-phenylsulfanyl)-piperidine-1-sulfonyl]-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester

HRID 599474
ノート
印刷プレビュー

反応式

HRID 599474 の反応式
[C:1]([C:5]1[CH:10]=[C:9]([S:11][CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[CH:8]=[C:7]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:6]=1[OH:22])([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.[CH3:32][O:33][C:34]([C:36]1[N:37]([CH3:45])[C:38]([S:41](Cl)(=[O:43])=[O:42])=[CH:39][CH:40]=1)=[O:35]>C1COCC1.C(OCC)(=O)C.O>[CH3:32][O:33][C:34]([C:36]1[N:37]([CH3:45])[C:38]([S:41]([N:15]2[CH2:16][CH2:17][CH:12]([S:11][C:9]3[CH:8]=[C:7]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:6]([OH:22])=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:10]=3)[CH2:13][CH2:14]2)(=[O:43])=[O:42])=[CH:39][CH:40]=1)=[O:35]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 81531DiisopropylethylamineHCID 2736899Methyl 5-(chlorosulfonyl)-1-methyl-1H-pyrrole-2-carboxylateHCID 86635428HCID 86635428、化合物

生成物 1

HCID 866354305-[4-(3,5-di-tert-butyl-4-hydroxy-phenylsulfanyl)-piperidine-1-sulfonyl]-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester収率 98.8%

試薬・触媒・溶媒 3

HCID 962Water
溶媒
HCID 8028Tetrahydrofuran溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

Alternatively, to a solution of 2,6-di-tert-butyl-4-(piperidin-4-ylsulfanyl)-phenol (Ex. 3d, 48.0 g, 0.15 moles) in THF (1000 mL) was added diisopropylethyl amine (39.0 mL, 0.22 moles) and methyl-5-(chlorosulfonyl)-1-methyl-1H-pyrrole-2-carboxylate (35.5 g, 0.15 moles) and the resulting solution was stirred at room temperature for 5 hours. Upon completion, as determined by HPLC, the reaction was diluted with ethyl acetate (500 mL) and water (500 mL). The layers were cut and the organic layer was washed with 1N HCl (500 mL) and 6% brine (2×500 mL), and concentrated under reduced pressure to afford 77.2 g (98.8%) of 5-[4-(3,5-di-tert-butyl-4-hydroxy-phenylsulfanyl)-piperidine-1-sulfonyl]-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester as a white solid, mp 185-187° C. 1H-NMR (400 MHz, CDCl3): δ 7.23 (s, 2H), 7.17 (d, 1H, J=1.6 Hz), 7.09 (d, 1H, J=2.0 Hz), 5.29 (s, 1H), 3.96 (s, 3H), 3.84 (s, 3H), 3.57 (m, 2H), 2.79 (m, 1H), 2.50 (m, 2H), 1.99 (m, 2H), 1.70 (m, 2H), 1.42 (s, 18H). HRMS (ESI) Calcd. for C26H38N2O5S2, 522.2222 (M+). Found: 522.2228. Anal. Calcd. for C26H38N2O5S2: C, 59.74; H, 7.33; N, 5.36; S, 12.27. Found: C, 59.48; H, 7.50; N, 5.22; S, 12.05.

後処理

  1. washthe organic layer was washed with 1N HCl (500 mL) and 6% brine (2×500 mL)
  2. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-d40585d96c60429b9fd181f3d30fbb3e
出典データセット
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07897776B2

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