Sodium Hydroxide → (+/-)-4-(4,4,4-Trifluoro-1-(quinolin-3-ylamino)butyl)benzoic acid

HRID 2281154ノート

反応式

HRID 2281154 の反応式
[F:1][C:2]([F:29])([F:28])[CH2:3][CH2:4][CH:5]([C:17]1[CH:27]=[CH:26][C:20]([C:21]([O:23]CC)=[O:22])=[CH:19][CH:18]=1)[NH:6][C:7]1[CH:8]=[N:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2.[OH-].[Na+]>CO.O1CCCC1>[F:29][C:2]([F:1])([F:28])[CH2:3][CH2:4][CH:5]([C:17]1[CH:18]=[CH:19][C:20]([C:21]([OH:23])=[O:22])=[CH:26][CH:27]=1)[NH:6][C:7]1[CH:8]=[N:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 86718839Ethyl (+/-)-4-(4,4,4-trifluoro-1-(quinolin-3-ylamino)butyl)benzoate

生成物 1

HCID 86718840(+/-)-4-(4,4,4-Trifluoro-1-(quinolin-3-ylamino)butyl)benzoic acid

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of ethyl (+/−)-4-(4,4,4-trifluoro-1-(quinolin-3-ylamino)butyl)benzoate (95 mg, 0.24 mmol) in methanol (1.2 mL) and tetrahydrofuran (1.2 mL) was added 1 N aq sodium hydroxide (1.2 mL, 1.2 mmol). After 17 hours, the solution was concentrated under reduced pressure to remove methanol and tetrahydrofuran. The mixture was then acidified to pH 5 with 1 N aq hydrochloric acid and diluted with sat. aq sodium chloride (20 mL). The mixture was extracted with ethyl acetate (3×20 mL). The combined organic layers were dried over Na2SO4 and filtered, and the filtrate was concentrated under reduced pressure to give (+/−)-4-(4,4,4-trifluoro-1-(quinolin-3-ylamino)butyl)benzoic acid. 1HNMR (400 MHz, CD3OD) δ 8.50 (br. s, 1 H), 8.02 (d, J=8.2 Hz, 2 H), 7.80-7.73 (m, 1 H), 7.57 (d, J=8.2 Hz, 2 H), 7.53-7.47 (m, 1 H), 7.40-7.32 (m, 2 H), 6.95 (d, J=2.5 Hz, 1 H), 4.73-4.64 (m, 1 H), 2.55-2.39 (m, 1 H), 2.39-2.22 (m, 1 H), 2.22-2.04 (m, 2 H).

後処理

  1. concentrationthe solution was concentrated under reduced pressure
  2. customto remove methanol and tetrahydrofuran
  3. additiondiluted with sat. aq sodium chloride (20 mL)
  4. extractionThe mixture was extracted with ethyl acetate (3×20 mL)
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-42c4074ea2c740b693b03d2da98f18a6
出典データセット
uspto-grants-2015_09
特許番号
US09139538B2

反応ノート

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