Chlorotrimethylsilane → (3S,4aR,4bS,6S,8R,8aR,10aR)-3-Furan-3-yl-4a,8a-dimethyl-1,5-dioxo-6-phenylcarbamoyloxy-dodecahydro-2-oxa-phenanthrene-8-carboxylic acid methyl ester

HRID 12319

反応式

HRID 12319 の反応式
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:18][C@H:17]([OH:19])[C:16](=[O:20])[C@H:15]2[C@@:6]1([CH3:28])[CH2:7][CH2:8][C@H:9]1[C@:14]2([CH3:21])[CH2:13][C@@H:12]([C:22]2[CH:26]=[CH:25][O:24][CH:23]=2)[O:11][C:10]1=[O:27])=[O:4].C[Si](Cl)(C)C.[C:34]1([N:40]=[C:41]=[O:42])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C(Cl)Cl>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:18][C@H:17]([O:19][C:41](=[O:42])[NH:40][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:16](=[O:20])[C@H:15]2[C@@:6]1([CH3:28])[CH2:7][CH2:8][C@@H:9]1[C@:14]2([CH3:21])[CH2:13][C@@H:12]([C:22]2[CH:26]=[CH:25][O:24][CH:23]=2)[O:11][C:10]1=[O:27])=[O:4]

参加物

5

反応物 3

HCID 6397ChlorotrimethylsilaneHCID 7672Phenyl isocyanateHCID 11395172(2S,4aS,6aR,7R,9S,10aS,10bR)-9-(hydroxy)-2-(3-furanyl)dodecahydro-6a,10b-dimethyl-4,10-dioxo-2H-naphtho[2,1-c]pyran-7-carboxylic acid methyl ester

生成物 1

HCID 11191431(3S,4aR,4bS,6S,8R,8aR,10aR)-3-Furan-3-yl-4a,8a-dimethyl-1,5-dioxo-6-phenylcarbamoyloxy-dodecahydro-2-oxa-phenanthrene-8-carboxylic acid methyl ester収率 14%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of 8a (0.06 g, 0.14 mmol), trimethylsilyl chloride (0.01 mL, 0.08 mmol) and phenylisocyanate (0.1 mL, 0.92 mmol) in CH2Cl2 was stirred at room temperature for 5 days. The reaction mixture was then washed with saturated NaHCO3 (10 mL) and H2O (10 mL) and dried (Na2SO4). The solvent was removed under reduced pressure to give a crude oil. The oil was purified by column chromatography (eluent: ethyl acetate/n-hexanes) to afford 22 (0.01 g, 14%) as a clear oil: 1H NMR (CDCl3): δ 1.15 (s, 3H); 1.48 (s, 3H); 1.52-1.72 (m, 3H); 1.82 (dd, 1H, 2.7, 10.2 1H); 2.03-2.20 (m, 1H); 2.22 (s, 1H); 2.24-2.48 (m, 2H); 2.54 (dd, Ja=5.1, Jb=13.5, 1H); 2.80 (dd, Ja=3.6, Jb=13.2, 1H); 3.75 (s, 3H); 5.21 (dd, Ja=7.8, Jb=12.3, 1H); 5.54 (dd, J=11.7, 1H); 6.40 (m, 1H), 6.69 (br s, 1H); 6.87 (br s, 1H); 7.12 (m, 2H); 7.28-7.45 (m, 5H).

後処理

  1. washThe reaction mixture was then washed with saturated NaHCO3 (10 mL) and H2O (10 mL)
  2. dry with materialdried (Na2SO4)
  3. customThe solvent was removed under reduced pressure
  4. customto give a crude oil
  5. customThe oil was purified by column chromatography (eluent: ethyl acetate/n-hexanes)

出典と根拠

ORDレコード
ord-9edfd93c7b884bb8a336fb912c356863
出典データセット
uspto-grants-2010_06
特許番号
US07728001B2

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