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Hydrochloric Acid → 2-Amino-2-(6-(4-phenoxyphenoxy)naphthalen-2-yl)propane-1,3-diol

HRID 1036506
ノート
印刷プレビュー

反応式

HRID 1036506 の反応式
CC1(C)[O:7][CH2:6][C:5]([NH2:32])([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:18][C:19]4[CH:24]=[CH:23][C:22]([O:25][C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=5)=[CH:21][CH:20]=4)[CH:14]=3)[CH:9]=2)[CH2:4][O:3]1.CO.Cl.O>>[NH2:32][C:5]([C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[CH:21][CH:20]=3)[CH:14]=2)[CH:9]=1)([CH2:4][OH:3])[CH2:6][OH:7]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 962WaterHCID 674244522,2-Dimethyl-5-(6-(4-phenoxyphenoxy)naphthalen-2-yl)-1,3-dioxan-5-amine

生成物 1

HCID 674236932-Amino-2-(6-(4-phenoxyphenoxy)naphthalen-2-yl)propane-1,3-diol収率 78.2%

反応条件

温度
90 °C

実験手順

2,2-Dimethyl-5-[6-(4-phenoxy-phenoxy)-naphthalen-2-yl]-1,3-dioxinan-5-ylamine (0.1241 g, 0.0002811 mol) was dissolved in methanol (3 mL, 0.07 mol) and a solution of 1 M of hydrogen chloride in water (5 mL, 0.005 mol) in a 40 mL reaction vial equipped with a magnetic stir bar. The vial was capped and heated at 90° C. overnight. TLC analysis showed that the reaction was complete. The reaction mixture was concentrated to dryness under reduced pressure. The resulting solid was dissolved in methylene chloride (5 mL) and washed with water then aqueous sodium carbonate. The combined organic layer was dried over magnesium sulfate, then concentrated under vacuum and purified by HPLC to give 88.3 mg of the title compound (78% yield). MS: m/z=424.45 [M+Na+]. 1H NMR (DMSO-d6) δ: 8.00 (s, 1H), 7.93 (d, J=8.7 Hz, 1H), 7.80 (d, J=8.7 Hz, 1H), 7.62-7.68 (m, 1H), 7.39-7.44 (m, 2H), 7.35-7.39 (m, 2H), 7.30 (dd, J=8.9, 2.5 Hz, 1H), 7.00-7.17 (m, 6H), 3.73 (d, J=3.8 Hz, 4H)

後処理

  1. customvial equipped with a magnetic stir bar
  2. customThe vial was capped
  3. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  4. dissolutionThe resulting solid was dissolved in methylene chloride (5 mL)
  5. washwashed with water
  6. dry with materialThe combined organic layer was dried over magnesium sulfate
  7. concentrationconcentrated under vacuum
  8. custompurified by HPLC

出典と根拠

ORDレコード
ord-b85d7aa72b134e81a8c944f4a08a05ce
出典データセット
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08546359B2

反応ノート

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