2-Aminoadamantane hydrochloride → N-(adamantane-2-yl)-1-(2-nitrophenylsulfonamido)cyclobutanecarboxyamide

HRID 1519079ノート

反応式

HRID 1519079 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:13][C:14]1([C:18](O)=O)[CH2:17][CH2:16][CH2:15]1)(=[O:12])=[O:11])([O-:3])=[O:2].Cl.[CH:22]12[CH2:31]C3[CH2:27][CH:28]([CH2:30]C(C3)[CH:23]1N)[CH2:29]2.F[P-](F)(F)(F)(F)F.N1([O:49][P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CC[N:62]([CH:66]([CH3:68])[CH3:67])[CH:63](C)C>C(Cl)Cl>[CH:68]12[CH2:31][CH:22]3[CH2:29][CH:28]([CH2:30][CH:67]([CH2:23]3)[CH:66]1[NH:62][C:63]([CH2:18][C:14]1([NH:13][S:10]([C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N+:1]([O-:3])=[O:2])(=[O:11])=[O:12])[CH2:15][CH2:16][CH2:17]1)=[O:49])[CH2:27]2

参加物

6

反応物 4

HCID 253312-Aminoadamantane hydrochlorideHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 712467071-(2-Nitrophenylsulfonamido)cyclobutanecarboxylic acid

生成物 1

HCID 131733091N-(adamantane-2-yl)-1-(2-nitrophenylsulfonamido)cyclobutanecarboxyamide収率 97%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

In a 10-mL flask, 1-(2-nitrophenylsulfonamido)cyclobutanecarboxylic acid (200 mg, 0.666 mmol), 2-adamantanamine hydrochloride (150 mg, 0.799 mmol), and BOP (295 mg, 0.667 mmol) were charged, and CH2Cl2 (3 ml) was charged, followed by stirring for 30 minutes at room temperature. DIPEA (0.28 ml, 1.60 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. The resultant mixture was purified with column chromatography (EA/n-Hex=1:2) to obtain N-(adamantane-2-yl)-1-(2-nitrophenylsulfonamido)cyclobutanecarboxyamide (282 mg, 97%).

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. customThe resultant mixture was purified with column chromatography (EA/n-Hex=1:2)

出典と根拠

ORDレコード
ord-67341d6b541d45e68a8f5098cf883529
出典データセット
uspto-grants-2015_07
特許番号
US09073830B2

反応ノート

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