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Triethylamine → Ethyl 5-(benzyloxy)-1-(methylsulfonyl)-2-(4-((methylsulfonyloxy)methyl)piperidin-1-yl)-6-oxo-1,6-dihydropyrimidine-4-carboxylate

HRID 1093118
ノート
印刷プレビュー

反応式

HRID 1093118 の反応式
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[NH:13][C:12]([N:16]2[CH2:21][CH2:20][CH:19]([CH2:22][OH:23])[CH2:18][CH2:17]2)=[N:11][C:10]=1[C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:29][S:30](Cl)(=[O:32])=[O:31].CCN(CC)CC>C1COCC1>[CH2:1]([O:8][C:9]1[C:14](=[O:15])[N:13]([S:30]([CH3:29])(=[O:32])=[O:31])[C:12]([N:16]2[CH2:17][CH2:18][CH:19]([CH2:22][O:23][S:30]([CH3:29])(=[O:32])=[O:31])[CH2:20][CH2:21]2)=[N:11][C:10]=1[C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
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 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 136061319Ethyl 5-(benzyloxy)-2-(4-(hydroxymethyl)piperidin-1-yl)-6-oxo-1,6-dihydropyrimidine-4-carboxylate

生成物 1

HCID 57904840Ethyl 5-(benzyloxy)-1-(methylsulfonyl)-2-(4-((methylsulfonyloxy)methyl)piperidin-1-yl)-6-oxo-1,6-dihydropyrimidine-4-carboxylate収率 99.2%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

実験手順

To a solution of ethyl 5-(benzyloxy)-2-(4-(hydroxymethyl)piperidin-1-yl)-6-oxo-1,6-dihydropyrimidine-4-carboxylate (0.814 g, 2.1 mmol) in THF (20 mL) was added methanesulfonyl chloride (0.327 mL, 4.20 mmol) followed by Et3N (0.732 mL, 5.25 mmol). The resulting mixture was stirred at room temperature for 2.5 h (white solids precipitated out over the reaction time). The mixture was diluted with ethyl acetate (50 mL) and washed with water followed by brine. The organic phase was dried (Na2SO4), filtered and concentrated to give the title compound as an amber oil (1.1320 g, 99% yield). 1H NMR (500 MHz, CDCl3) δ: 7.44 (2H, d, J=7.32 Hz), 7.39-7.32 (3H, m), 4.98 (2H, s), 4.67-4.64 (2H, m), 4.35 (2H, q, J=7.1 Hz), 4.09 (2H, d, J=6.4 Hz), 3.46 (3H, s), 3.02 (3H, s), 2.91 (2H, td, J=12.9, 2.4 Hz), 2.08-2.00 (1H, m), 1.86-1.84 (2H, m), 1.35-1.28 (5H, m). LCMS (M+H) calcd for C22H30N3O9S2: 544.14; found: 544.30.

後処理

  1. customprecipitated out over the reaction time)
  2. additionThe mixture was diluted with ethyl acetate (50 mL)
  3. washwashed with water
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-ad40a6e587e445c48b965c097c0e9d1b
出典データセット
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08129398B2

反応ノート

読み込み中…

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