Diisopropylethylamine → E-3-[4'-hydroxybiphenyl-3-yl]-N-hydroxyacrylamide

HRID 12993

反応式

HRID 12993 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10](/[CH:14]=[CH:15]/[C:16]([OH:18])=O)[CH:9]=2)=[CH:4][CH:3]=1.CN(C([O:26][N:27]1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.Cl.NO>CN(C=O)C>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10](/[CH:14]=[CH:15]/[C:16]([NH:27][OH:26])=[O:18])[CH:9]=2)=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 443297Hydroxyamine hydrochlorideHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 22475282E-3-(4'-hydroxybiphenyl-3-yl)-acrylic acid

生成物 1

HCID 42632370E-3-[4'-hydroxybiphenyl-3-yl]-N-hydroxyacrylamide収率 32.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

70 mg (0.29 mmol) of E-3-(4′-hydroxybiphenyl-3-yl)-acrylic acid were dissolved under nitrogen in 3 ml of DMF, then 109 mg (0.29 mmol) of HBTU and 100 μL (0.57 mmol) of DIPEA were added at 0° C. After 5 min hydroxylamine hydrochloride (20 mg, 0.29 mmol) was added and the mixture was stirred at 0° C. for 10 min., then at room temperature for 4 h. DMF was removed under reduced pressure and the residue was washed with water to obtain, after filtration, 73 mg of a crude product. Purification by flash chromatography on KH2PO4 buffered silicagel using as eluent CH2Cl2/MeOH 95:5 afforded 24 mg of the title compound as a white solid. M.p. 127-128° C. Rf=0.26 (Merck silica gel 60F254, CH2Cl2:/MeOH 90:10)

後処理

  1. waitat room temperature for 4 h
  2. customDMF was removed under reduced pressure
  3. washthe residue was washed with water
  4. customto obtain
  5. filtrationafter filtration, 73 mg of a crude product
  6. customPurification by flash chromatography on KH2PO4 buffered silicagel

出典と根拠

ORDレコード
ord-310f30a16ec54f1182a25511c29bcf0a
出典データセット
uspto-grants-2010_06
特許番号
US07728039B2

関連ノート

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