Water → HCID 70183914, 화합물

HRID 355576노트

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HRID 355576 반응식
[ClH:1].[Cl:2][C:3]1[CH:4]=[C:5]([CH2:10][C@@H:11]([O:15][C:16]([C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=2)=[O:17])[C@@H:12]([NH2:14])[CH3:13])[CH:6]=[CH:7][C:8]=1Cl.[CH:28]12[C:40](=[O:41])[O:39][C:37](=[O:38])[CH:29]1[CH:30]1[C:35](=[O:36])[O:34][C:32](=[O:33])[CH:31]12.[CH2:42](N(CC)CC)C.[N+](=C)=[N-].[OH2:52]>CCOCC.C(OCC)(=O)C.C(O)=O>[CH3:42][O:52][C:35]([C@H:30]1[C@@H:29]([C:37]([NH:14][C@H:12]([C@H:11]([O:15][C:16]([C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=2)=[O:17])[CH2:10][C:5]2[CH:6]=[CH:7][C:8]([Cl:1])=[C:3]([Cl:2])[CH:4]=2)[CH3:13])=[O:38])[C@H:28]([C:40]([OH:39])=[O:41])[C@@H:31]1[C:32]([OH:34])=[O:33])=[O:36]

참가 물질

9

반응물 5

HCID 962WaterHCID 8471TriethylamineHCID 9550DiazomethaneHCID 1072801,2,3,4-Cyclobutanetetracarboxylic dianhydrideHCID 70182797(1S,2R)-3-(3,4-dichlorophenyl)-1-methyl-2-(2-naphthoyloxy)propylamine hydrochloride

생성물 1

HCID 70183914HCID 70183914, 화합물

시약·촉매·용매 3

HCID 284Formic Acid용매HCID 3283Diethyl Ether용매HCID 8857Ethyl Acetate용매

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온도
22 °C

실험 절차

To a suspension of (1S,2R)-3-(3,4-dichlorophenyl)-1-methyl-2-(2-naphthoyloxy)propylamine hydrochloride (42.5 mg, 0.10 mmol), prepared by the procedures described in European Patent Application EP 611749, published Aug. 24, 1994, and incorporated herein by reference, 1,2,3,4-cyclobutanetetracarboxylic dianhydride (100 mg, 0.50 mmol) in 1:1 etheracetonitrile (10 mL) at -78° C. was added triethylamine (15 mg, 0.15 mmol). The reaction mixture was allowed to warm to 22° C. overnight and then cooled with an ice-water bath. Diazomethane in ether was added to it until the solution remained slightly yellow. Formic acid (0.5 mL) was added immediately, followed by ethyl acetate (60 mL) and water (5 mL). The organic layer was washed with water (5 mL) and brine (5 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated. The crude product was purified with column chromatography eluting with ethyl acetate (80 mL), followed by 95:5:1 ethyl acetate-methanol-formic acid to give the title compound (51.3 mg). The proton NMR showed about a 1:1 ratio of rotomers. 1H NMR (300 MHz, DMSO-D6) δ 8.59, 8.55 (s, 1H), 8.37, 8.27 (d, 1H), 8.16-7.89 (m, 4H), 7.70-7.45 (m, 3H), 7.25 (t, 1H), 5.33 & 5.19 (m, 1H), 4.10 (m, 1H), 3.62 (s, 3H), 3.57-3.45 (m, 3H), 3.35 (m, 1H), 3.08 (m, 1H), 2.97 (m, 1H), 1.09, 1.07 (s, 3H). MS (FAB+) m/e 616 [35Cl, M+H]+.

후처리

  1. customprepared by the procedures
  2. temperaturecooled with an ice-water bath
  3. washThe organic layer was washed with water (5 mL) and brine (5 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified with column chromatography
  8. washeluting with ethyl acetate (80 mL)

출처 및 근거

ORD 기록
ord-9fa6be139ae24e56b5595dc7a239c92f
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05831115

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