Acetic Acid → cis-4-(3,5-Bis-trifluoromethyl-benzylamino)-6-hydroxy-7-methoxy-2-methyl-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester

HRID 279379노트

반응식

HRID 279379 반응식
[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([OH:18])=[C:13]([O:16][CH3:17])[CH:14]=2)[C@H:9]([NH2:19])[CH2:8][C@@H:7]1[CH3:20])=[O:5])[CH3:2].[F:21][C:22]([F:36])([F:35])[C:23]1[CH:24]=[C:25]([CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1)[CH:26]=O.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[K+].[K+]>ClCCl.O>[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([OH:18])=[C:13]([O:16][CH3:17])[CH:14]=2)[C@H:9]([NH:19][CH2:26][C:25]2[CH:28]=[C:29]([C:31]([F:33])([F:34])[F:32])[CH:30]=[C:23]([C:22]([F:21])([F:35])[F:36])[CH:24]=2)[CH2:8][C@@H:7]1[CH3:20])=[O:5])[CH3:2]

참가 물질

8

반응물 5

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 1362473,5-Bis(trifluoromethyl)benzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 69832492cis-4-Amino-6-hydroxy-7-methoxy-2-methyl-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester

생성물 1

HCID 86755994cis-4-(3,5-Bis-trifluoromethyl-benzylamino)-6-hydroxy-7-methoxy-2-methyl-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester수율 65.5%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

To a stirred suspension of cis-4-amino-6-hydroxy-7-methoxy-2-methyl-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester (387 mg, 1.38 mmol) in dichloromethane (9 mL) was added 3,5-bis(trifluoromethyl)benzaldehyde (225 μL, 1.38 mmol), followed by acetic acid (80 μL, 1.4 mmol). The reaction was stirred at room temperature for 1 h, then sodium triacetoxyborohydride (440 mg, 2.08 mmol) was added. The reaction was stirred at room temperature for 5 h. Water (5 mL) was added, and the mixture was slowly basified to pH 10 with solid potassium carbonate. The mixture was then extracted with ethyl acetate (3×10 mL), the combined organic phases were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo to give 680 mg crude product. Purification by silica gel chromatography using 0-25% ethyl acetate/hexanes as eluent afforded 458 mg of the title compound (65%).

후처리

  1. stirringThe reaction was stirred at room temperature for 5 h
  2. extractionThe mixture was then extracted with ethyl acetate (3×10 mL)
  3. washthe combined organic phases were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give 680 mg crude product
  8. customPurification by silica gel chromatography

출처 및 근거

ORD 기록
ord-a5be883114f54ebda5125a9fd49913ed
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06362198B1

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