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(2-Methylpropyl)boronic acid → {(1R)-2-cyclobutyl-1-[((2S)-2-{[(6-phenoxypyridin-3-yl)sulfonyl]amino}-3-phenylpropanoyl)amino]ethyl}boronic acid

HRID 1182696
ノート
印刷プレビュー

反応式

HRID 1182696 の反応式
[CH:1]1([CH2:5][C@H:6]([NH:20][C:21](=[O:47])[C@@H:22]([NH:30][S:31]([C:34]2[CH:35]=[N:36][C:37]([O:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)=[CH:38][CH:39]=2)(=[O:33])=[O:32])[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[B:7]2[O:11][C@@H]3C[C@@H]4C[C@H]([C@]3(C)[O:8]2)C4(C)C)[CH2:4][CH2:3][CH2:2]1.CC(C)CB(O)O>CO>[CH:1]1([CH2:5][C@@H:6]([B:7]([OH:11])[OH:8])[NH:20][C:21](=[O:47])[C@@H:22]([NH:30][S:31]([C:34]2[CH:35]=[N:36][C:37]([O:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)=[CH:38][CH:39]=2)(=[O:33])=[O:32])[CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:2][CH2:3][CH2:4]1
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 2734395(2-Methylpropyl)boronic acidHCID 68527475(2S)-N-{(1R)-2-cyclobutyl-1-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}-2-{[(6-phenoxypyridin-3-yl)sulfonyl]amino}-3-phenylpropanamide

生成物 1

HCID 45255496{(1R)-2-cyclobutyl-1-[((2S)-2-{[(6-phenoxypyridin-3-yl)sulfonyl]amino}-3-phenylpropanoyl)amino]ethyl}boronic acid収率 74.8%

試薬・触媒・溶媒 1

HCID 887
Methanol
溶媒

実験手順

Into a 20 mL vial was added (25)-N-{(1R)-2-cyclobutyl-1-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}-2-{[(6-phenoxypyridin-3-yl)sulfonyl]amino}-3-phenylpropanamide (31.2 mg, 0.047 mmol), (2-methylpropyl)boronic acid (10.4 mg) 1N hydrochloric acid (0.107 mmol), methanol (0.285 mL and hexanes (0.285 mL.) The mixture was stirred at room temperature overnight, then the hexane layer was separated and discarded. The remaining solvent was removed in vacuo and the residue purified by preparative TLC on silica plates using 10% MeOH in CH2Cl2 to give 18.4 mg (74% yield) of desired product as a white solid. 1H NMR (CD3OD, 300 MHz, δ): 8.36 (s, 1H); 7.95-7.84 (m, 1H); 7.52-7.39 (m, 2H); 7.33-7.06 (m, 10H); 6.95-6.83 (m, 1H); 4.25-4.13 (m, 1H); 3.09-2.94 (m, 1H); 2.93-2.78 (m, 1H); 2.46-2.32 (m, 1H); 2.26-1.93 (m, 3H); 1.92-1.71 (m, 2H); 1.64-1.37 (m, 3H); 1.37-1.22 (m, 1H).

後処理

  1. customthe hexane layer was separated
  2. customThe remaining solvent was removed in vacuo
  3. customthe residue purified by preparative TLC on silica plates

出典と根拠

ORDレコード
ord-07ecea87ecc24f45b4f7044a3174f50e
出典データセット
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08664200B2

反応ノート

読み込み中…

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