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Chlorosulfamic acid → HCID 12020528、化合物

HRID 2304379
ノート
印刷プレビュー

反応式

HRID 2304379 の反応式
[H-].[Na+].[CH2:3]([NH:7][C:8]([C:10]1[C@:11]2([CH2:27][CH2:26][C@H:25]3[C@@H:16]([CH2:17][CH2:18][C:19]4[CH:20]=[C:21]([OH:28])[CH:22]=[CH:23][C:24]=43)[C@@H:13]2[CH2:14][CH:15]=1)[CH3:12])=[O:9])[CH2:4][CH2:5][CH3:6].Cl[S:30]([NH2:33])(=[O:32])=[O:31].C(=O)(O)[O-].[Na+]>CN(C=O)C>[S:30](=[O:32])(=[O:31])([O:28][C:21]1[CH:22]=[CH:23][C:24]2[C@@H:25]3[C@H:16]([C@H:13]4[C@@:11]([CH2:27][CH2:26]3)([CH3:12])[C:10]([C:8](=[O:9])[NH:7][CH2:3][CH2:4][CH2:5][CH3:6])=[CH:15][CH2:14]4)[CH2:17][CH2:18][C:19]=2[CH:20]=1)[NH2:33]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 24499Chlorosulfamic acidHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 12019734HCID 12019734、化合物

生成物 1

HCID 12020528HCID 12020528、化合物収率 96%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Sodium hydride (20 mg) was added to a solution comprising 73 mg of compound 10a in 2 ml of anhydrous DMF at 0° C. The solution was stirred for 25 minutes and 126 mg of chlorosulfonamide was added in one portion. The solution was then stirred at room temperature for 2 hours. Ice and saturated sodium bicarbonate solution was added to the reaction mixture. The precipitate formed was filtered and washed with water. The residue was purified by chromatography on silica gel (CHCl3:methanol, 50:1), yielding compound 11a (85 mg, 96%). FAB-MS mn/z 433 (M+H)+; 1H NMR (270 MHz, DMSO-d6) δ 0.88 (t, 3H, J=7.5 Hz, CH2CH3), 0.91 (s, 3H, CH3), 3.08(dt, 2H, J=5.6, 6.6 Hz, NHCH2), 6.34 (s, 1H, 16-CH), 6.97 (s, 1H, ArH), 7.01 (dd, 1H, J=2.6, 8.6 Hz, ArH), 7.33 (d, 1H, J=8.6 Hz, ArH), 7.71 (t, 1H, J=5.6 Hz, NHCH2), 7.88 (s, 2H, NH2).

後処理

  1. customat 0° C
  2. stirringThe solution was then stirred at room temperature for 2 hours
  3. customThe precipitate formed
  4. filtrationwas filtered
  5. washwashed with water
  6. customThe residue was purified by chromatography on silica gel (CHCl3:methanol, 50:1)

出典と根拠

ORDレコード
ord-fc45a57cf3634f59818420ea3c93532a
出典データセット
uspto-grants-2002_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06436918B1

反応ノート

読み込み中…

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