Ethanol → HCID 178464723、化合物

HRID 1036404

反応式

HRID 1036404 の反応式
[CH3:1][C@@:2]1([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:18][C@H:19]4[CH2:24][CH2:23][C@@H:22]([CH3:25])[CH2:21][CH2:20]4)[CH:14]=3)[CH:9]=2)[CH2:6][O:5]C(=O)[NH:3]1.C(O)C.O.[OH-].[Li+]>O>[NH2:3][C@@:2]([C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:18][C@H:19]3[CH2:20][CH2:21][C@@H:22]([CH3:25])[CH2:23][CH2:24]3)[CH:14]=2)[CH:9]=1)([CH3:1])[CH2:6][OH:5]

参加物

5

反応物 3

HCID 702EthanolHCID 168937Lithium hydroxide, monohydrateHCID 178421574HCID 178421574、化合物

生成物 1

HCID 178464723HCID 178464723、化合物収率 6%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

To a solution of (R)-4-Methyl-4-[6-(cis4-methyl-cyclohexyloxy)-naphthalen-2-yl]-oxazolidin-2-one (0.4420 g, 0.001302 mol) in ethanol (5.00 mL, 0.0856 mol) in a capped 40 mL vial was added 4.2 M Lithium hydroxide, monohydrate in water (2.8 mL). The mixture was heated overnight at 80° C. TLC analysis showed the reaction was complete. The mixture was concentrated to dryness under vacuum. Methylene chloride (5 mL) and water (5 mL) were added and the layers were separated (2×). The organic layer was concentrated under vacuum and purified by HPLC to give 0.0233 g of the title compound (6% yield). MS: m/z=297.29 [M−NH2]+. 1H NMR (400 MHz, MeOD) δ 0.98 (d, J=6.02 Hz, 3H), 1.40-1.51 (m, 2H), 1.51-1.60 (m, 3H), 1.64-1.74 (m, 2H), 1.79 (s, 3H), 2.03-2.14 (m, 2H), 3.83 (d, J=11.55 Hz, 1H), 3.93 (d, J=11.55 Hz, 1H), 4.69-4.77 (m, 1H), 7.23 (dd, J=8.91, 2.38 Hz, 1H), 7.27 (d, J=2.51 Hz, 1H), 7.53 (dd, J=8.78, 2.01 Hz, 1H), 7.79-7.89 (m, 3H)

後処理

  1. concentrationThe mixture was concentrated to dryness under vacuum
  2. additionMethylene chloride (5 mL) and water (5 mL) were added
  3. customthe layers were separated (2×)
  4. concentrationThe organic layer was concentrated under vacuum
  5. custompurified by HPLC

出典と根拠

ORDレコード
ord-e4605061053247c280ea13972fb55ad0
出典データセット
uspto-grants-2013_10
特許番号
US08546359B2

関連ノート

読み込み中…