Triethylamine → Ethyl 2-[4-methoxy-3-({[4-(trifluoromethyl)benzoyl]amino}methyl)benzyl]butanoate

HRID 1826086노트

반응식

HRID 1826086 반응식
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1.C(N(CC)CC)C.C(Cl)(=O)OCC.Cl.[CH2:28]([CH:30]([CH2:36][C:37]1[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[C:39]([CH2:45][NH2:46])[CH:38]=1)[C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH3:29]>ClCCl>[CH2:28]([CH:30]([CH2:36][C:37]1[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[C:39]([CH2:45][NH:46][C:7](=[O:9])[C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:13])[F:12])=[CH:11][CH:10]=2)[CH:38]=1)[C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH3:29]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 99664-(Trifluoromethyl)benzoic acidHCID 10928Ethyl chloroformateHCID 22139981Ethyl 2-[(3-aminomethyl-4-methoxyphenyl)-methyl]butyrate hydrochloride

생성물 1

HCID 11004633Ethyl 2-[4-methoxy-3-({[4-(trifluoromethyl)benzoyl]amino}methyl)benzyl]butanoate수율 93.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 4-(trifluoromethyl)benzoic acid (114 mg, 0.600 mmol) and triethylamine (0.21 mL, 1.51 mmol) in dichloromethane (3 mL), ethyl chlorocarbonate (0.063 mL, 0.659 mmol) was added under stirring and cooling with ice, and the mixture was stirred for 20 minutes. Next, after ethyl 2-ethyl-3-[3-(aminomethyl)-4-methoxyphenyl]propanoate hydrochloride (200 mg, 0.663 mmol) was added, the mixture was stirred for 1 hour under cooling with ice and for 3 hours at room temperature. Dichloromethane (20 mL) was added to the reaction mixture, which was washed with 1 mol/L hydrochloric acid, saturated aqueous solution of sodium hydrogencarbonate and brine, dried over anhydrous sodium sulfate, and then concentrated. The residue was purified by silica gel column chromatography (eluent: n-hexane:ethyl acetate=4:1 v/v) to afford 245 mg (93%) of the title compound as colorless crystals.

후처리

  1. temperaturecooling with ice
  2. stirringthe mixture was stirred for 20 minutes
  3. stirringthe mixture was stirred for 1 hour
  4. washwas washed with 1 mol/L hydrochloric acid, saturated aqueous solution of sodium hydrogencarbonate and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (eluent: n-hexane:ethyl acetate=4:1 v/v)

출처 및 근거

ORD 기록
ord-a4c6184cdd674d08b7da1aa97b5c970f
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07049342B2

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