Hydrochloric Acid → Solabegron

HRID 1053608ノート

反応式

HRID 1053608 の反応式
O.[OH-].[Li+].C[O:5][C:6]([C:8]1[CH:9]=[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([NH:20][CH2:21][CH2:22][NH:23][CH2:24][C@@H:25]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[CH:28]=3)[OH:26])[CH:15]=2)[CH:11]=[CH:12][CH:13]=1)=[O:7].Cl>O.C(O)C>[Cl:33][C:29]1[CH:28]=[C:27]([C@@H:25]([OH:26])[CH2:24][NH:23][CH2:22][CH2:21][NH:20][C:16]2[CH:15]=[C:14]([C:10]3[CH:11]=[CH:12][CH:13]=[C:8]([C:6]([OH:7])=[O:5])[CH:9]=3)[CH:19]=[CH:18][CH:17]=2)[CH:32]=[CH:31][CH:30]=1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 9845280HCID 9845280、化合物

生成物 1

HCID 9887812Solabegron収率 41.36%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

A solution of 10% lithium hydroxide monohydrate in water (2 mL) was added to a solution of (R)-3′-{2-[2-(3-chloro-phenyl)-2-hydroxy-ethylamino]-ethylamino}-biphenyl-3-carboxylic acid methyl ester (50 mg, 0.12 mmol, 1.00 equiv) in ethanol (4 mL). The solution was stirred at ambient temperature for about 16 hours, and then the pH value of the solution was adjusted to 7-8 with concentrated hydrogen chloride. After concentrating the solution in vacuo, the resulting crude residue was purified by prep-HPLC to give the title product of as a white solid (20 mg; yield=41.36%). LC-MS: m/z=411 (MH)+. Retention time: 1.69 minute. [α]20.4D −20° (c=0.075, MeOH). [a]=−20° (c=0.075 g/100 ml in methanol, T=20.4). 1H NMR (300 MHz, CD3OD) δ: 8.22 (s, 1H), 7.92 (d, J=7.8 Hz, 1H), 7.62 (d, J=7.8 Hz, 1H), 7.47 (s, 1H), 7.29-7.38 (m, 4H), 7.20 (t, J=8.1 Hz, 1H), 6.97 (m, 2H), 6.68 (d, J=1.5 Hz, 1H), 5.00 (m, 1H), 3.56 (t, J=6.0 Hz, 2H), 3.23-3.33 (m, 3H), 3.12 (m, 1H).

後処理

  1. concentrationAfter concentrating the solution in vacuo
  2. customthe resulting crude residue was purified by prep-HPLC

出典と根拠

ORDレコード
ord-3cf084c399b04f5ba66a4439b1c6e074
出典データセット
uspto-grants-2016_07
特許番号
US09394239B2

反応ノート

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