Hydrochloric Acid → (+/-)-4-[(3,3-Dimethyl-cyclobutyl)-(3-methyl-quinolin-2-ylamino)-methyl]-benzoic acid

HRID 2281128ノート

反応式

HRID 2281128 の反応式
C([O:3][C:4](=[O:30])[C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH:24]2[CH2:27][C:26]([CH3:29])([CH3:28])[CH2:25]2)[NH:12][C:13]2[C:22]([CH3:23])=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=2)=[CH:7][CH:6]=1)C.[OH-].[Na+].Cl>O1CCCC1.CO>[CH3:28][C:26]1([CH3:29])[CH2:25][CH:24]([CH:11]([NH:12][C:13]2[C:22]([CH3:23])=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=2)[C:8]2[CH:7]=[CH:6][C:5]([C:4]([OH:30])=[O:3])=[CH:10][CH:9]=2)[CH2:27]1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 71243836(+/-)-4-[(3,3-Dimethyl-cyclobutyl)-(3-methyl-quinolin-2-ylamino)-methyl]-benzoic acid ethyl ester2 回

生成物 1

HCID 71243837(+/-)-4-[(3,3-Dimethyl-cyclobutyl)-(3-methyl-quinolin-2-ylamino)-methyl]-benzoic acid収率 91.5%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

(+/−)-4-[(3,3-dimethyl-cyclobutyl)-(3-methyl-quinolin-2-ylamino)-methyl]-benzoic acid ethyl ester (Intermediate 25) (43 mg, 0.11 mmol) was dissolved in tetrahydrofuran (3 mL) and methanol (1 mL), and 1.0 M NaOH (2 mL) was added. This was stirred at 50° C. at first as a suspension then as a clear solution for 4 h before cooling to room temperature. 1 N HCl was added until the solution was pH 5. This was extracted twice with ethyl acetate and the combined organics were dried over MgSO4. The solution was concentrated in vacuo to give (+/−)-4-[(3,3-dimethyl-cyclobutyl)-(3-methyl-quinolin-2-ylamino)-methyl]-benzoic acid (37.7 mg) as a white solid. MS (M+1): 375.1.

後処理

  1. temperatureas a clear solution for 4 h before cooling to room temperature
  2. extractionThis was extracted twice with ethyl acetate
  3. dry with materialthe combined organics were dried over MgSO4
  4. concentrationThe solution was concentrated in vacuo

出典と根拠

ORDレコード
ord-25b76d30cbfb4109b258b862266f0ca0
出典データセット
uspto-grants-2015_09
特許番号
US09139538B2

反応ノート

読み込み中…