Triethylamine → Ethyl 7-[({[(2S)-1'-{2-[(5R)-3-[3,5-bis(trifluoromethyl)benzoyl]-5-(4-fluorophenyl)-1,3-oxazolidin-5-yl]ethyl}-2,3-dihydrospiro[indene-1,4'-piperidin]-2-yl]oxy}acetyl)(methyl)amino]heptanoate

HRID 446562노트

반응식

HRID 446562 반응식
[F:1][C:2]([F:49])([F:48])[C:3]1[CH:4]=[C:5]([CH:41]=[C:42]([C:44]([F:47])([F:46])[F:45])[CH:43]=1)[C:6]([N:8]1[CH2:12][C@@:11]([CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][C:25]3([C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[CH2:29][C@@H:28]3[O:36]CC(O)=O)[CH2:24][CH2:23]2)([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[O:10][CH2:9]1)=[O:7].[CH2:50]([N:52]([CH2:55][CH3:56])[CH2:53][CH3:54])C.ClC(OCC(C)C)=[O:59].CNCC[CH2:69][CH2:70][CH2:71][CH2:72][C:73]([O:75][CH2:76][CH3:77])=[O:74].C(=O)([O-])O.[Na+]>ClCCl>[F:47][C:44]([F:45])([F:46])[C:42]1[CH:41]=[C:5]([CH:4]=[C:3]([C:2]([F:49])([F:48])[F:1])[CH:43]=1)[C:6]([N:8]1[CH2:12][C@@:11]([CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][C:25]3([C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[CH2:29][C@@H:28]3[O:36][CH2:54][C:53]([N:52]([CH3:50])[CH2:55][CH2:56][CH2:69][CH2:70][CH2:71][CH2:72][C:73]([O:75][CH2:76][CH3:77])=[O:74])=[O:59])[CH2:24][CH2:23]2)([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[O:10][CH2:9]1)=[O:7]

참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 516892Sodium BicarbonateHCID 86663420{[(2S)-1'-{2-[(5R)-3-[3,5-Bis(trifluoromethyl)benzoyl]-5-(4-fluorophenyl)-1,3-oxazolidin-5-yl]ethyl}-2,3-dihydrospiro[indene-1,4'-piperidin]-2-yl]oxy}acetic acidHCID 86663458Ethyl 7-(methylamino)heptanoate

생성물 1

HCID 86663457Ethyl 7-[({[(2S)-1'-{2-[(5R)-3-[3,5-bis(trifluoromethyl)benzoyl]-5-(4-fluorophenyl)-1,3-oxazolidin-5-yl]ethyl}-2,3-dihydrospiro[indene-1,4'-piperidin]-2-yl]oxy}acetyl)(methyl)amino]heptanoate수율 79%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

The compound (625 mg, 0.901 mmol) obtained in Example 1j was dissolved in dichloromethane (9 mL), triethylamine (0.376 mL, 2.70 mmol) and isobutyl chloroformate (183 μL, 1.35 mmol) were added under ice cooling, and the mixture was stirred at the same temperature. The compound (467 mg, 2.70 mmol) obtained in Example 68a was added under ice cooling, and then the temperature was increased to room temperature. After the reaction was completed, a saturated aqueous sodium hydrogencarbonate solution was added, and the mixture was extracted with dichloromethane (×2). The resulting organic layer was dried with anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by NH silica gel column chromatography (a elution solvent, ethyl acetate) to give the title compound (615 mg; yield, 79%).

후처리

  1. extractionthe mixture was extracted with dichloromethane (×2)
  2. dry with materialThe resulting organic layer was dried with anhydrous sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe resulting residue was purified by NH silica gel column chromatography (a elution solvent, ethyl acetate)

출처 및 근거

ORD 기록
ord-df1a81ab01114d1293e99b34a2462de2
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476253B2

반응 노트

불러오는 중…