Hydrochloric Acid → [(1R)-1-({[(2-bromobenzoyl)amino]acetyl}amino)-3-methylbutyl]boronic acid

HRID 539594

反応式

HRID 539594 の反応式
[Br:1][C:2]1[CH:32]=[CH:31][CH:30]=[CH:29][C:3]=1[C:4]([NH:6][CH2:7][C:8]([NH:10][C@H:11]([B:16]1[O:20][C@@H]2C[C@@H]3C[C@H]([C@]2(C)[O:17]1)C3(C)C)[CH2:12][CH:13]([CH3:15])[CH3:14])=[O:9])=[O:5].Cl.B([O-])OCC(C)C>CO.CCCCCC>[Br:1][C:2]1[CH:32]=[CH:31][CH:30]=[CH:29][C:3]=1[C:4]([NH:6][CH2:7][C:8]([NH:10][C@H:11]([B:16]([OH:20])[OH:17])[CH2:12][CH:13]([CH3:15])[CH3:14])=[O:9])=[O:5]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 673667952-bromo-N-[2-({(1R)-3-methyl-1-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborol-2-yl]butyl}amino)-2-oxoethyl]benzamideHCID 178450000HCID 178450000、化合物

生成物 1

HCID 25183866[(1R)-1-({[(2-bromobenzoyl)amino]acetyl}amino)-3-methylbutyl]boronic acid収率 73%

試薬・触媒・溶媒 1

HCID 21896459Hexane methanol溶媒

実験手順

To a solution of 2-bromo-N-[2-({(1R)-3-methyl-1-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborol-2-yl]butyl}amino)-2-oxoethyl]benzamide (0.220 g, 0.44 mmol) in methanol/hexane (1:1) (2.2 mL) were added 1N HCl (1 mL, 1.0 mmol) and isobutyl boronate (0.078 g, 0.76 mmol). The reaction mixture was allowed to stir overnight. The reaction mixture was concentrated and purified by reverse phase HPLC to give [(1R)-1-({[(2-bromobenzoyl)amino]acetyl}amino)-3-methylbutyl]boronic acid (0.119 g, 73%).

後処理

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by reverse phase HPLC

出典と根拠

ORDレコード
ord-d77bba02e4f74e2dae46d8cd23aae4c6
出典データセット
uspto-grants-2014_10
特許番号
US08871745B2

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