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Hydrochloric Acid → N-{[4-N-(benzhydryloxycarbonyl)-cytosin-1-yl]-acetyl}-N-[2-(2-nitro-benzenesulfonylamino)-ethyl]-glycine

HRID 1794945
ノート
印刷プレビュー

反応式

HRID 1794945 の反応式
C([O:3][C:4](=[O:49])[CH2:5][N:6]([C:22](=[O:48])[CH2:23][N:24]1[CH:47]=[CH:46][C:28]([NH:29][C:30]([O:32][CH:33]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:31])=[N:27][C:25]1=[O:26])[CH2:7][CH2:8][NH:9][S:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20])(=[O:12])=[O:11])C.[OH-].[Li+].Cl.[Cl-].[Na+]>C1COCC1.O>[CH:33]([O:32][C:30]([NH:29][C:28]1[CH:46]=[CH:47][N:24]([CH2:23][C:22]([N:6]([CH2:7][CH2:8][NH:9][S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N+:19]([O-:21])=[O:20])(=[O:11])=[O:12])[CH2:5][C:4]([OH:49])=[O:3])=[O:48])[C:25](=[O:26])[N:27]=1)=[O:31])([C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1
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 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 5234Sodium ChlorideHCID 22222376N-{[4-N-(Benzhydryloxycarbonyl)-cytosin-1-yl]-acetyl}-N-[2-(2-nitro-benzenesulfonylamino)-ethyl]-glycine ethyl ester

生成物 1

HCID 22222393N-{[4-N-(benzhydryloxycarbonyl)-cytosin-1-yl]-acetyl}-N-[2-(2-nitro-benzenesulfonylamino)-ethyl]-glycine収率 78%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of N-{[4-N-(Benzhydryloxycarbonyl)-cytosin-1-yl]-acetyl}-N-[2-(2-nitro-benzenesulfonylamino)-ethyl]-glycine ethyl ester (1.91 g, 2.75 mmol) in THF (10 mL) was added a solution of lithium hydroxide (290 mg, 6.9 mmol) in water (9 mL) at 10° C. After stirring for 1.5 h, the reaction mixture was acidified to pH=3˜4 by adding 1 N HCl solution. The aqueous layer was saturated with sodium chloride and organic layer was separated. The aqueous layer was extracted with THF (15 mL×2). The combined organic layer was dried over sodium sulfate and filtered. The filtrate was concentrated and triturated with ethyl alcohol to precipitate solid. The precipitated solid was filtered off, washed with water, and dried in vacuo to give the tilted product as a white solid (1.42 g, 78%). 1H-NMR (500 MHz; DMSO-d6) δ 8.25˜7.80 (m, 5H), 7.50˜7.25 (m, 10H), 6.94 (d, 0.6H), 6.92 (d, 0.4H), 6.79 (1H, s), 4.78 (s, 1.2H), 4.60 (s, 0.8H), 4.22 (s, 0.8H), 3.94 (s, 1.2H), 3.50 (t, 1.2H), 3.35 (t, 0.8H), 3.24 (q, 1.2H), 3.02 (q, 0.8H).

後処理

  1. customwas separated
  2. extractionThe aqueous layer was extracted with THF (15 mL×2)
  3. dry with materialThe combined organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customtriturated with ethyl alcohol
  7. customto precipitate solid
  8. filtrationThe precipitated solid was filtered off
  9. washwashed with water
  10. customdried in vacuo

出典と根拠

ORDレコード
ord-fabdec24943d40c3a1d4e6e326d388f3
出典データセット
uspto-grants-2006_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07022851B2

反応ノート

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