Ethyl Acetate → (2s,3r)-n-(2-((3-Pyridinyl)methyl)-1-azabicyclo[2.2.2]oct-3-yl)benzofuran-2-carboxamide d-mandelate salt

HRID 45293ノート

反応式

HRID 45293 の反応式
[C:1]([OH:11])(=[O:10])[C@@H:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3].[N:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][C@H:19]2[C@H:24]([NH:25][C:26]([C:28]3[O:29][C:30]4[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=4[CH:32]=3)=[O:27])[CH:23]3[CH2:37][CH2:38][N:20]2[CH2:21][CH2:22]3)[CH:13]=1.C(OCC)(=O)C>C(O)C>[C:1]([OH:11])(=[O:10])[C@@H:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3].[N:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][C@H:19]2[C@H:24]([NH:25][C:26]([C:28]3[O:29][C:30]4[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=4[CH:32]=3)=[O:27])[CH:23]3[CH2:37][CH2:38][N:20]2[CH2:21][CH2:22]3)[CH:13]=1

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 11914(-)-Mandelic acidHCID 25147644Bradanicline

生成物 1

HCID 131729023(2s,3r)-n-(2-((3-Pyridinyl)methyl)-1-azabicyclo[2.2.2]oct-3-yl)benzofuran-2-carboxamide d-mandelate salt収率 62.4%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
5 °C

実験手順

D-Mandelic acid (52.6 mg, 0.346 mmol) was added to a solution of (2S,3R)—N-(2-((3-pyridinyl)methyl)-1-azabicyclo[2.2.2]oct-3-yl)benzofuran-2-carboxamide (125 mg, 0.346 mmol) in hot ethanol (1 mL). Dilution with ethyl acetate (4 mL) and cooling failed to produce a precipitate. The volatiles were removed by rotary evaporation, and the residue (white foam) was dissolved in hot isopropanol (0.5 mL). Cooling to 5° C. produced white crystals which were collected by suction filtration. Vacuum oven drying (18 h at 45° C.) gave 111 mg (62.4% yield) of light beige solid, mp 188.5-193° C. 1H NMR (300 MHz, D2O) δ 8.33 (s, 1H), 7.83 (s, 1H), 7.67 (d, 1H), 7.60 (d, 1H), 7.27 (m, 8H, includes mandelic acid), 7.12 (s, 1H), 7.01 (m, 1H), 4.85 (s, 1H, mandelic acid), 4.10 (d, 1H), 3.75 (m, 1H), 3.48 (m, 2H), 3.00-3.40 (m, 4H), 1.75-2.15 (m, 5H).

後処理

  1. customto produce a precipitate
  2. customThe volatiles were removed by rotary evaporation
  3. dissolutionthe residue (white foam) was dissolved in hot isopropanol (0.5 mL)
  4. customproduced white crystals which
  5. filtrationwere collected by suction filtration
  6. customVacuum oven drying (18 h at 45° C.)
  7. customgave 111 mg (62.4% yield) of light beige solid, mp 188.5-193° C

出典と根拠

ORDレコード
ord-aa2a0b682bb1496a8329333e78f9d132
出典データセット
uspto-grants-2013_09
特許番号
US08541446B2

反応ノート

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