Hydrochloric Acid → (3r)-1-Butyl-2,5-dioxo-3-((1r)-1-hydroxy-1-cyclohexylmethyl)-9-(4-(4-(n-hydroxycarbamoyl)phenyloxy)phenylmethyl)-1,4,9-triazaspiro[5.5]undecane.hydrochloride

HRID 855778ノート

反応式

HRID 855778 の反応式
[ClH:1].[CH2:2]([N:6]1[C:11]2([CH2:16][CH2:15][N:14]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][C:25]4[CH:30]=[CH:29][C:28]([C:31]([OH:33])=O)=[CH:27][CH:26]=4)=[CH:20][CH:19]=3)[CH2:13][CH2:12]2)[C:10](=[O:34])[NH:9][C@H:8]([C@H:35]([OH:42])C2CCCCC2)[C:7]1=[O:43])[CH2:3][CH2:4][CH3:5].COC([O:49][NH2:50])(C)C.C(N(C(C)C)CC)(C)C.Cl.C(N=C=NCCCN(C)C)C.ON1[C:77]2[CH:78]=[CH:79][CH:80]=[CH:81][C:76]=2N=N1.Cl>CN(C)C=O.O>[ClH:1].[CH2:2]([N:6]1[C:11]2([CH2:16][CH2:15][N:14]([CH2:17][C:18]3[CH:19]=[CH:20][C:21]([O:24][C:25]4[CH:26]=[CH:27][C:28]([C:31](=[O:33])[NH:50][OH:49])=[CH:29][CH:30]=4)=[CH:22][CH:23]=3)[CH2:13][CH2:12]2)[C:10](=[O:34])[NH:9][C@H:8]([C@H:35]([OH:42])[CH:76]2[CH2:77][CH2:78][CH2:79][CH2:80][CH2:81]2)[C:7]1=[O:43])[CH2:3][CH2:4][CH3:5]

参加物

9

反応物 6

HCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 6918686Aplaviroc HydrochlorideHCID 13608208O-(2-Methoxyisopropyl)hydroxylamine

生成物 1

HCID 23577391(3r)-1-Butyl-2,5-dioxo-3-((1r)-1-hydroxy-1-cyclohexylmethyl)-9-(4-(4-(n-hydroxycarbamoyl)phenyloxy)phenylmethyl)-1,4,9-triazaspiro[5.5]undecane.hydrochloride収率 94.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a suspension of the compound prepared in Example 9(54) (120 mg) and (1-methoxyisopropyl)oxyamine (31 mg) in dimethylformamide (1.6 ml) was added diisopropylethylamine (68 μl), 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide.hydrochloride (56 mg) and 1-hydroxybenztriazole (40 mg). The reaction mixture was stirred for 1 hour at room temperature. The reaction mixture was added 1N hydrochloric acid (2 ml) and stirred for 15 minutes at room temperature. The reaction mixture was diluted with water and extracted with ethyl acetate. The extract was washed with water, saturated aqueous solution of sodium bicarbonate and saturated aqueous solution of sodium chloride and the obtained residue was dried over anhydrous sodium sulfate and concentrated. To a solution of the obtained residue in methanol was added 4N hydrogen chloride/ethyl acetate solution and concentrated. The obtained residue was washed with ethyl acetate to give the title compound (116 mg) having the following physical data.

後処理

  1. stirringstirred for 15 minutes at room temperature
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water, saturated aqueous solution of sodium bicarbonate and saturated aqueous solution of sodium chloride
  4. dry with materialthe obtained residue was dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. additionTo a solution of the obtained residue in methanol was added 4N hydrogen chloride/ethyl acetate solution
  7. concentrationconcentrated
  8. washThe obtained residue was washed with ethyl acetate

出典と根拠

ORDレコード
ord-ded80229f25545fbb5b4feb23e278c1d
出典データセット
uspto-grants-2007_08
特許番号
US07262193B2

反応ノート

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