Hydrochloric Acid → Solabegron

HRID 1624204ノート

反応式

HRID 1624204 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([OH:29])[CH2:9][NH:10][CH2:11][CH2:12][NH:13][C:14]2[CH:15]=[C:16]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([OH:28])=[O:27])[CH:21]=3)[CH:17]=[CH:18][CH:19]=2)[CH:5]=[CH:6][CH:7]=1.O.[OH-].[Li+].COC(C1C=C(C2C=CC=C(NCCNC[C@@H](C3C=CC=C(Cl)C=3)O)C=2)C=CC=1)=O.Cl>O.C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([OH:29])[CH2:9][NH:10][CH2:11][CH2:12][NH:13][C:14]2[CH:15]=[C:16]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([OH:28])=[O:27])[CH:21]=3)[CH:17]=[CH:18][CH:19]=2)[CH:5]=[CH:6][CH:7]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 6433124HCID 6433124、化合物HCID 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

3′-(2 (2 (3 chlorophenyl)-2-hydroxyethylamino)ethylamino)biphenyl-3-carboxylic acid (solabegron): 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). [α]=−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-9e1bc82d065d4a7f94ced999a0784e6e
出典データセット
uspto-grants-2014_07
特許番号
US08778998B2

反応ノート

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