Nitrogen → Methyl (2S)-2-acetamido-3-(4-[9-anthracenyl]phenyl)-propanoate

HRID 37770

반응식

HRID 37770 반응식
[C:1]([NH:4][C@@H:5]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([Sn](C)(C)C)=[CH:13][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])(=[O:3])[CH3:2].Br[C:22]1[C:23]2[C:28]([CH:29]=[C:30]3[C:35]=1[CH:34]=[CH:33][CH:32]=[CH:31]3)=[CH:27][CH:26]=[CH:25][CH:24]=2.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.N#N>CN(C=O)C.C(OCC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CO.C(Cl)Cl>[C:1]([NH:4][C@@H:5]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:22]2[C:35]3[C:30]([CH:29]=[C:28]4[C:23]=2[CH:24]=[CH:25][CH:26]=[CH:27]4)=[CH:31][CH:32]=[CH:33][CH:34]=3)=[CH:13][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])(=[O:3])[CH3:2]

참가 물질

9

반응물 4

HCID 947NitrogenHCID 740629-BromoanthraceneHCID 80271Tri-o-tolylphosphineHCID 42597285methyl (2S)-2-acetamido-3-(4-trimethylstannylphenyl)propanoate

생성물 1

HCID 42597519Methyl (2S)-2-acetamido-3-(4-[9-anthracenyl]phenyl)-propanoate수율 67%

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매HCID 21226129Dichloromethane methanol용매

반응 조건

온도
70 °C

실험 절차

A solution of 95 (192 mg, 0.50 mmol), 9-bromoanthracene (141 mg, 0.55 mmol), palladium acetate (6 mg, 0.025 mmol), and tri-o-tolylphosphine (15 mg, 0.05 mmol) in DMF (2 mL) was flushed with N2 for 15 min then heated to 70° C. and allowed to stir for 16 h. The reaction was diluted with diethyl ether (20 mL) and washed with water (5×20 mL), dried and evaporated. The crude product was purified by flash column chromatography (15% EtOAc/hexane then 5% MeOH/DCM) to yield the title compound (133 mg, 0.33 mmol, 67%) as an orange oil. [α]D27 +66.9 (c. 0.1, CHCl3). 1H NMR (CDCl3, 300 MHz): δ 8.48 (s, 1H, ArH10″); 8.03 (dd, J=0.9, 8.7 Hz, 2H, ArH3″ and ArH6″); 7.63 (dd, J=0.6, 9.0 Hz, 2H, ArH8″ and ArH1″); 7.45 (m, 2H, ArH4″ and ArH5″); 7.36 (m, 6H, ArH2″ and ArH7″, 4×ArH″); 5.40 (d, J=7.8 Hz, 1H, NH); 5.04 (m, 1H, H2); 3.79 (s, 3H, OCH3); 3.32 (dd, J=5.7, 13.8 Hz, 1H, H3a); 3.25 (dd, J=6.3, 13.8 Hz, 1H, H3b); 2.08 (s, 3H, COCH3). Mass Spectrum (CI, +ve) m/z 398 (100%) [MH+]. HRMS calcd for C26H23NO3 397.1678, found 397.1675.

후처리

  1. washwashed with water (5×20 mL)
  2. customdried
  3. customevaporated
  4. customThe crude product was purified by flash column chromatography (15% EtOAc/hexane

출처 및 근거

ORD 기록
ord-d38b64fa795c4fcf8881dbb8e7dbca6f
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524657B2

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