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

HRID 2281128노트

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HRID 2281128 반응식
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

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 71243836(+/-)-4-[(3,3-Dimethyl-cyclobutyl)-(3-methyl-quinolin-2-ylamino)-methyl]-benzoic acid ethyl ester2회

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

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온도
50 °C

실험 절차

(+/−)-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.

후처리

  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

출처 및 근거

ORD 기록
ord-25b76d30cbfb4109b258b862266f0ca0
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09139538B2

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