Diisopropylethylamine → 2-(4-acetylphenylsulfonamido)-N-(5-hydroxyadamantane-2-yl)-2-methylpropanamide

HRID 1519108ノート

反応式

HRID 1519108 の反応式
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]([CH3:19])([CH3:18])[C:15]([OH:17])=O)(=[O:12])=[O:11])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[OH:20][C:21]12[CH2:30][CH:25]3[CH2:26][CH:27]([CH2:29][CH:23]([CH:24]3[NH2:31])[CH2:22]1)[CH2:28]2.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C>C(Cl)Cl>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([S:10]([NH:13][C:14]([CH3:19])([CH3:18])[C:15]([NH:31][CH:24]2[CH:23]3[CH2:29][CH:27]4[CH2:28][C:21]([OH:20])([CH2:30][CH:25]2[CH2:26]4)[CH2:22]3)=[O:17])(=[O:11])=[O:12])=[CH:8][CH:9]=1)(=[O:3])[CH3:2]

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 28574474-Aminoadamantan-1-olHCID 210825082-(4-Acetylphenylsulfonamido)-2-methylpropionic acid

生成物 1

HCID 712469482-(4-acetylphenylsulfonamido)-N-(5-hydroxyadamantane-2-yl)-2-methylpropanamide収率 69%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

2-(4-acetylphenylsulfonamido)-2-methylpropionic acid (109 mg, 0.38 mmol), 5-hydroxy-2-adamantanamine (127 mg, 0.76 mmol), and BOP (168 mg, 0.38 mmol) were charged, and CH2Cl2 (5 ml) was added thereto, followed by stirring for 30 minutes at room temperature. DIPEA (0.18 ml, 1.14 mmol) was added thereto, followed by stirring at room temperature for 12 hours. After the reaction was completed, the organic layer was separated using CH2Cl2 and H2O, dried with MgSO4, and filtered. Then, through vacuum distillation, the solvent was removed, and the resultant product was purified with column chromatography to obtain 2-(4-acetylphenylsulfonamido)-N-(5-hydroxyadamantane-2-yl)-2-methylpropanamide (110 mg, 0.25 mmol, 69%).

後処理

  1. stirringby stirring at room temperature for 12 hours
  2. customthe organic layer was separated
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. distillationThen, through vacuum distillation
  6. customthe solvent was removed
  7. customthe resultant product was purified with column chromatography

出典と根拠

ORDレコード
ord-4f92304798e84fe79f85525937c6bded
出典データセット
uspto-grants-2015_07
特許番号
US09073830B2

反応ノート

読み込み中…