Water → Tert-butyl cis-2-(6-amino-3-bromo-5-(2-phenylpropan-2-ylaminocarbonyl)pyridin-2-ylamino)cyclohexylcarbamate

HRID 1620052ノート

反応式

HRID 1620052 の反応式
[Br:1]N1C(=O)CCC1=O.CN(C=O)C.[NH2:14][C:15]1[N:20]=[C:19]([NH:21][C@H:22]2[CH2:27][CH2:26][CH2:25][CH2:24][C@H:23]2[NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH:18]=[CH:17][C:16]=1[C:36]([NH:38][C:39]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)([CH3:41])[CH3:40])=[O:37].O>C(OCC)(=O)C>[NH2:14][C:15]1[N:20]=[C:19]([NH:21][C@H:22]2[CH2:27][CH2:26][CH2:25][CH2:24][C@H:23]2[NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[C:18]([Br:1])=[CH:17][C:16]=1[C:36]([NH:38][C:39]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)([CH3:40])[CH3:41])=[O:37]

参加物

6

反応物 4

HCID 962WaterHCID 6228DimethylformamideHCID 67184N-bromobutanimideHCID 86683853Tert-butyl cis-2-(6-amino-5-(2-phenylpropan-2-ylaminocarbonyl)pyridin-2-ylamino)cyclohexylcarbamate

生成物 1

HCID 86683852Tert-butyl cis-2-(6-amino-3-bromo-5-(2-phenylpropan-2-ylaminocarbonyl)pyridin-2-ylamino)cyclohexylcarbamate収率 100.7%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

N-bromosuccinimide (22 mg) was added to a DMF (5 ml) solution containing tert-butyl cis-2-(6-amino-5-(2-phenylpropan-2-ylaminocarbonyl)pyridin-2-ylamino)cyclohexylcarbamate (60 mg) at 0° C., followed by stirring for 1 hour. Water and ethyl acetate were added to the reaction mixture. The organic layer was collected, washed with saturated saline, and dried over anhydrous sodium sulfate, and then the solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel chromatography (silica gel:silica gel 60 (spherical shape) (Kanto Chemical Co., Inc.); hexane:ethyl acetate=4:1 to 3:1), and a white solid of tert-butyl cis-2-(6-amino-3-bromo-5-(2-phenylpropan-2-ylaminocarbonyl)pyridin-2-ylamino)cyclohexylcarbamate (68 mg) was thus obtained.

後処理

  1. customThe organic layer was collected
  2. washwashed with saturated saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled away under reduced pressure
  5. customThe obtained residue was purified by silica gel chromatography (silica gel:silica gel 60 (spherical shape) (Kanto Chemical Co., Inc.); hexane:ethyl acetate=4:1 to 3:1)

出典と根拠

ORDレコード
ord-e4aaaeb0182c4fee8695d07ae781344f
出典データセット
uspto-grants-2014_07
特許番号
US08772320B2

反応ノート

読み込み中…