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

HRID 7903

반응식

HRID 7903 반응식
[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]

참가 물질

10

반응물 5

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

생성물 1

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

시약·촉매·용매 4

HCID 142844-(Dimethylamino)pyridine촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-bd4a17db7fd44b94ad9c395a089d4e4a
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087628B2

연결된 노트

불러오는 중…