1,2-Dichloroethane → HCID 178445682, 화합물

HRID 1992803노트

반응식

HRID 1992803 반응식
[C:1]([C@@H:5]1[CH2:10][CH2:9][C@H:8]([NH:11][C:12]([C:14]2[N:18]([CH2:19][C:20]3[CH:28]=[CH:27][C:23](C(O)=O)=[CH:22][N:21]=3)[N:17]=[C:16]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[C:31]([Cl:36])[CH:30]=3)[CH:15]=2)=[O:13])[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].C1C=NC2N(O)N=NC=2C=1.C([O:51][C:52](=[O:56])[CH2:53][CH2:54][NH2:55])(C)(C)C.CCN(C(C)C)C(C)C.C(Cl)CCl.[C:70](O)(C(F)(F)F)=[O:71]>CN(C=O)C.C(OCC)(=O)C.C(Cl)Cl>[C:1]([C@@H:5]1[CH2:10][CH2:9][C@H:8]([NH:11][C:12]([C:14]2[N:18]([CH2:19][C:20]3[N:21]=[CH:22][C:23]([C:70]([NH:55][CH2:54][CH2:53][C:52]([OH:51])=[O:56])=[O:71])=[CH:27][CH:28]=3)[N:17]=[C:16]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[C:31]([Cl:36])[CH:30]=3)[CH:15]=2)=[O:13])[CH2:7][CH2:6]1)([CH3:2])([CH3:4])[CH3:3]

참가 물질

10

반응물 6

HCID 111,2-DichloroethaneHCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 4192171tert-Butyl 3-aminopropanoateHCID 178445683HCID 178445683, 화합물

생성물 1

HCID 178445682HCID 178445682, 화합물

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of the intermediate from step H (65 mg, 0.122 mmol) in DMF (2 mL) was added HOAt (25 mg, 0.184 mmol), β-alanine-tert-butyl ester (34 mg, 0.184 mmol), DIEA (64 μL, 0.37 mmol) and EDC (36 mg, 0.184 mmol). After stirring the reaction at room temperature for 18 hours, the reaction was diluted with ethyl acetate and washed with 1N HCl , saturated NaHCO3 and saturated NaCl solution. The organic layer was dried over anhydrous Na2SO4 filtered and concentrated in vacuo. The residue was purified by flash chromatography using 30% ethyl acetate-hexanes. Colorless oil was obtained. This material was dissolved in DCM (2 mL) and TFA was added (2 mL). After 1 hour the reaction mixture was concentrated in vacuo and azeotroped with toluene (3×) to give the title compound as a solid. 1H NMR (DMSO, 500 MHz): 8.88 (d, J=1.4 Hz, 1H), 8.72 (t, J=5.4 Hz, 1H), 8.2 (d, J=8.7 Hz, 1H), 8.14 (dd, J=2.3, 8.2 Hz, 1H), 8.02 (d, J=1.8 Hz, 1H), 7.81 (dd, J=2.0, 8.5 Hz, 1H), 7.71 (d, J=8.4 Hz, 1H), 7.48 (s, 1H), 7.15 (d, J=8.0 Hz, 1H), 5.85 (s, 2H), 3.48 (q, J=6.9 Hz, 2H), 1.83 (bd, J=12.6 Hz, 2H), 1.45 (m, 4H), 1.25 (m, 2H), 0.98 (m, 1H), 0.83 (s, 9H). LC-MS=3.99 min, (M+H)=600.2.

후처리

  1. customthe reaction at room temperature for 18 hours
  2. washwashed with 1N HCl , saturated NaHCO3 and saturated NaCl solution
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography
  7. customColorless oil was obtained
  8. concentrationAfter 1 hour the reaction mixture was concentrated in vacuo
  9. customazeotroped with toluene (3×)

출처 및 근거

ORD 기록
ord-1d453662620e4b2ab59a86d589522244
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07649009B2

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