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

Sodium Bicarbonate → {4-[(2R)-2-Hydroxy-2-(4-hydroxy-3-methanesulfonylamino-phenyl)-ethylamino]-piperidin-1-yl}-benzoic acid ethyl ester

HRID 1061309
ノート
印刷プレビュー

反応式

HRID 1061309 の反応式
C(OC([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]2)=[CH:8][CH:7]=1)=O)C.[NH2:19][CH2:20][C@@H:21]([C:23]1[CH:24]=[CH:25][C:26]([OH:34])=[C:27]([NH:29][S:30]([CH3:33])(=[O:32])=[O:31])[CH:28]=1)[OH:22].C(O[BH-](O[C:45](=[O:47])[CH3:46])OC(=O)C)(=O)C.[Na+].[C:49](=O)(O)[O-:50].[Na+]>CN(C)C=O.C(O)(=O)C>[CH2:45]([O:47][C:49](=[O:50])[C:8]1[CH:7]=[CH:6][CH:11]=[CH:10][C:9]=1[N:12]1[CH2:13][CH2:14][CH:15]([NH:19][CH2:20][C@H:21]([OH:22])[C:23]2[CH:24]=[CH:25][C:26]([OH:34])=[C:27]([NH:29][S:30]([CH3:33])(=[O:32])=[O:31])[CH:28]=2)[CH2:16][CH2:17]1)[CH3:46]
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 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 12047933(R)-N-(5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl)methanesulfonamideHCID 12717442Ethyl 4-(4-oxopiperidin-1-yl)benzoate

生成物 1

HCID 69654607{4-[(2R)-2-Hydroxy-2-(4-hydroxy-3-methanesulfonylamino-phenyl)-ethylamino]-piperidin-1-yl}-benzoic acid ethyl ester収率 50%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 6228Dimethylformamide溶媒

実験手順

1-(4-Ethoxycarbonylphenyl)-4-piperidone (Taylor, E. C., Skotnicki, J. S. Synthesis, 1981, 606) (0.29 g, 1.2 mmol) and N-[5-(2-amino-(1R)-1-hydroxy-ethyl)-2-hydroxy-phenyl]-methanesulfonamide (which was obtained in Example 10) (0.29 g, 1.2 mmol) were mixed in dimethylformamide (10 mL) and then treated with sodium triacetoxyborohydride (1.01 g, 4.7 mmol) and acetic acid (0.5 mL). After stirring at room temperature under a nitrogen atmosphere for 15 hours the mixture was poured into a saturated aqueous sodium bicarbonate. The precipitate which was formed was collected and purified by silica gel chromatography (methanol/methylene chloride) to give the titled compound as a white solid (0.28 g, 50%); mp >95° C. (decomposed); 1H NMR (300 MHz, DMSO-d6) δ 1.28 (t, J=7.1 Hz, 3H), 1.30-1.55 (m, 2H), 1.80-1.95 (m, 2H), 2.55-3.50 (m, 5H), 2.92 (s, 3H), 3.75-3.90 (m, 2H), 4.22 (q, J=7.1 Hz, 2H), 6.82 (d, J=8.2Hz, 1H), 6.95 (d, J=8.9Hz, 2H), 7.00 (dd, J=8.2, 1.9Hz, 1H), 7.18 (d, J=1.9 Hz, 1H), 7.75 (d, J=8.9 Hz, 2H); MS (ES) m/z: 478.0 (MH+); HRMS Calcd. for C23H32N3O6S(MH+): 478.2006. Found: 478.2000.

後処理

  1. customThe precipitate which was formed
  2. customwas collected
  3. custompurified by silica gel chromatography (methanol/methylene chloride)

出典と根拠

ORDレコード
ord-28fff3b780224bea8eb9d10e2aad63dc
出典データセット
uspto-grants-2003_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06525202B2

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