Triethylamine → (S)-2-(1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl)-7-nitroisoindolin-1-one

HRID 1019520ノート

反応式

HRID 1019520 の反応式
CO[C:3](=[O:15])[C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:13]Br.[CH2:16]([O:18][C:19]1[CH:20]=[C:21]([C@H:27]([NH2:33])[CH2:28][S:29]([CH3:32])(=[O:31])=[O:30])[CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[CH3:17].C(N(CC)CC)C>CN(C=O)C.CCOCC>[CH2:16]([O:18][C:19]1[CH:20]=[C:21]([C@H:27]([N:33]2[CH2:13][C:5]3[C:4](=[C:9]([N+:10]([O-:12])=[O:11])[CH:8]=[CH:7][CH:6]=3)[C:3]2=[O:15])[CH2:28][S:29]([CH3:32])(=[O:31])=[O:30])[CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[CH3:17]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 11282264(1S)-1-(3-Ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethylamineHCID 21708527Methyl 2-(bromomethyl)-6-nitrobenzoate

生成物 1

HCID 58224189(S)-2-(1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl)-7-nitroisoindolin-1-one収率 54.1%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

実験手順

A solution of 2-bromomethyl-6-nitro-benzoic acid methyl ester (4.0 g, 14.6 mmol), (1S)-1-(3-ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethylamine (4.0 g, 14.6 mmol) and triethylamine (4.4 mL, 31.6 mmol) in DMF (40 mL) was heated at 80° C.-90° C. for 1 day. The solvent was removed in vacuo to give an oil. The oil was extracted with ethyl acetate (150 mL) and HCl (2N, 50 mL). The organic layer was washed with HCl (2N, 2×50 mL), water (2×50 mL), brine (2×50 mL) and dried over MgSO4. The solvent was removed in vacuo to give a yellow oil. The oil was slurried in ether (50 mL) to give a suspension. The suspension was filtered and washed with ether to give 2-[(1S)-1-(3-ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethyl]-7-nitro-2,3-dihydro-isoindol-1-one as a yellow solid (3.43 g, 54% yield): 1H NMR (CDCl3) δ 1.5 (t, J=7 Hz, 3H, CH3), 2.99 (s, 3H, CH3), 3.69 (dd, J=5, 15 Hz, 1H, CHH), 3.86 (s, 3H, CH3), 4.07 (q, J=7 Hz, 2H, CH2), 4.27 (dd, J=11, 15 Hz, 1H, CHH), 4.30 (d, J=17 Hz, 1H, NCHH), 4.54 (d, J=17 Hz, 1H, NCHH), 5.70 (dd, J=5, 10 Hz, 1H, NCH), 6.85 (d, J=8 Hz, 1H, Ar), 6.94-7.00 (m, 2H, Ar), 7.58-7.76 (m, 3H, Ar).

後処理

  1. customThe solvent was removed in vacuo
  2. customto give an oil
  3. extractionThe oil was extracted with ethyl acetate (150 mL) and HCl (2N, 50 mL)
  4. washThe organic layer was washed with HCl (2N, 2×50 mL), water (2×50 mL), brine (2×50 mL)
  5. dry with materialdried over MgSO4
  6. customThe solvent was removed in vacuo
  7. customto give a yellow oil
  8. customto give a suspension
  9. filtrationThe suspension was filtered
  10. washwashed with ether

出典と根拠

ORDレコード
ord-0b94e5cae27b44b390294e24374a301c
出典データセット
uspto-grants-2014_05
特許番号
US08716252B2

反応ノート

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