Heptanol → [(1R)-1-({[(2,3-difluorobenzoyl)amino]acetyl}amino)-3-methylbutyl]boronic acid

HRID 2118268

反応式

HRID 2118268 の反応式
[F:1][C:2]1[C:32]([F:33])=[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].C(O)CCCCCC.B([O-])OCC(C)C>CO>[F:1][C:2]1[C:32]([F:33])=[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]([CH3:14])[CH3:15])=[O:9])=[O:5]

参加物

5

反応物 3

HCID 8129HeptanolHCID 673690412,3-difluoro-N-[2-({(1R)-3-methyl-1-[(3aR,4R,6R,7aS)-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 25022369[(1R)-1-({[(2,3-difluorobenzoyl)amino]acetyl}amino)-3-methylbutyl]boronic acid

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of 2,3-difluoro-N-[2-({(1R)-3-methyl-1-[(3aR,4R,6R,7aS)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborol-2-yl]butyl}amino)-2-oxoethyl]benzamide (0.536 g, 1.2 mmol) in methanol/1N HCl (1:1) (1.5 mL) were added heptanol (1 mL) and isobutyl boronate (0.207 g, 2.0 mmol). The reaction mixture was allowed to stir overnight. The heptanol layer was separated and the methanol/HCl layer was concentrated. The crude product was purified by reverse phase HPLC to give [(1R)-1-({[(2,3-difluorobenzoyl)amino]acetyl}amino)-3-methylbutyl]boronic acid.

後処理

  1. customThe heptanol layer was separated
  2. concentrationthe methanol/HCl layer was concentrated
  3. customThe crude product was purified by reverse phase HPLC

出典と根拠

ORDレコード
ord-2b3568a48b094f03a1e358bac8d1fa41
出典データセット
uspto-grants-2008_10
特許番号
US07442830B1

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