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

HRID 1519108

반응식

HRID 1519108 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-4f92304798e84fe79f85525937c6bded
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073830B2

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