2-Hydrazinopyridine → 1-(3,3-Dimethyl-2-oxo-pentanoyl)-pyrrolidine-2-carboxylic acid N'-pyridine-2-yl-hydrazide

HRID 7903

反応式

HRID 7903 の反応式
[O:1]=[C:2]([N:10]1[CH2:14][CH2:13][CH2:12][C@H:11]1[C:15]([OH:17])=O)[C:3](=[O:9])[C:4]([CH3:8])([CH3:7])[CH2:5][CH3:6].COC(=O)[C@@H]1CCCN1.[NH:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=1)[NH2:28].C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C1C=CN=CC=1)C.C1COCC1.C(OCC)(=O)C.O>[N:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=1[NH:27][NH:28][C:15]([CH:11]1[CH2:12][CH2:13][CH2:14][N:10]1[C:2](=[O:1])[C:3](=[O:9])[C:4]([CH3:7])([CH3:8])[CH2:5][CH3:6])=[O:17]

参加物

10

反応物 5

HCID 786452-HydrazinopyridineHCID 81531DiisopropylethylamineHCID 853477Methyl L-prolinateHCID 2733179PyBroPHCID 9837656Gpi-1485

生成物 1

HCID 102684911-(3,3-Dimethyl-2-oxo-pentanoyl)-pyrrolidine-2-carboxylic acid N'-pyridine-2-yl-hydrazide

試薬・触媒・溶媒 4

HCID 142844-(Dimethylamino)pyridine触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of (2S)-1-(1,2-dioxo-3,3-dimethylpentyl)-2-pyrrolidine-carboxylic acid (482 mg, 2 mmol), prepared from L-proline methyl ester according to the procedure described in WO 96/40633, 2-hydrazinopyridine (364 mg, 2 mmol), PyBrop (932 mg, 2 mmol), DMAP (4-dimethyaminopyridine, 122 mg) and DIEA (4 mL) in THF (dry, 50 mL) was stirred at room temperature for 24 h. Water and ethyl acetate were added. The organic phase was washed with ammonium chloride solution, followed by brine, and dried with MgSO4. Column chromatography (silica gel, ethyl acetate:methanol=10:0.5) gave a colorless oil; 490 mg (74%); MS (m/z) 333 (M+1); 1H NMR (d6-DMSO) δ0.85 (t, J=8 Hz, 3 H), 1.21 (s, 3 H), 1.23 (s, 3 H), 1.7 (m, 2 H), 1.90 (m, 1 H), 2.10 (m, 2 H), 2.35 (m, 1 H), 3.49 (t, J=8 Hz, 2 H), 4.62 (m, 1 H), 6.76 (m, 2 H), 7.51 (t, J=6 Hz, 1 H), 8.14 (d, J=6 Hz, 1 H).

後処理

  1. washThe organic phase was washed with ammonium chloride solution
  2. dry with materialdried with MgSO4
  3. customColumn chromatography (silica gel, ethyl acetate:methanol=10:0.5) gave a colorless oil

出典と根拠

ORDレコード
ord-bd4a17db7fd44b94ad9c395a089d4e4a
出典データセット
uspto-grants-2006_08
特許番号
US07087628B2

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