Hydrochloric Acid → Solabegron

HRID 1624204노트

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HRID 1624204 반응식
[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

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 6433124HCID 6433124, 화합물HCID 9845280HCID 9845280, 화합물

생성물 1

HCID 9887812Solabegron수율 41.36%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-9e1bc82d065d4a7f94ced999a0784e6e
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08778998B2

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