Triethylamine → HCID 86602061, 화합물

HRID 1295378노트

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HRID 1295378 반응식
C(N(CC)CC)C.[F:8][C:9]([F:25])([F:24])[C:10]1[CH:11]=[C:12]([CH:20]([NH:22][CH3:23])[CH3:21])[CH:13]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:15]=1.ClC(Cl)(O[C:30](=[O:36])OC(Cl)(Cl)Cl)Cl.[C:38]([O:42][C:43](=[O:57])[NH:44][C@@:45]12[CH2:50][CH:49]1[CH2:48][NH:47][C@H:46]2[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)([CH3:41])([CH3:40])[CH3:39].C(N(C(C)C)CC)(C)C>C(Cl)Cl.C(#N)C>[C:38]([O:42][C:43](=[O:57])[NH:44][C@@:45]12[CH2:50][CH:49]1[CH2:48][N:47]([C:30](=[O:36])[N:22]([C@H:20]([C:12]1[CH:13]=[C:14]([C:16]([F:17])([F:18])[F:19])[CH:15]=[C:10]([C:9]([F:8])([F:24])[F:25])[CH:11]=1)[CH3:21])[CH3:23])[C@H:46]2[C:51]1[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1)([CH3:41])([CH3:39])[CH3:40]

참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 220173563,5-Bis(trifluoromethyl)-alpha,N-dimethylbenzylamineHCID 69336084HCID 69336084, 화합물

생성물 1

HCID 86602061HCID 86602061, 화합물

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

To a round bottom flask was added methylene chloride (8 mL), triethylamine (0.87 mL, 6.3 mmol), and [(SR)-1-(3,5-bis-trifluoromethyl-phenyl)-ethyl]-methyl-amine (0.49 g, 1.6 mmol. The mixture was cooled to 0° C. and triphosgene (0.18 g, 0.61 mmol) in methylene chloride (3 mL) was added dropwise. The clear solution was stirred for 16 hours at room temperature. To the reaction mixture was added racemic Intermediate 48, one enantiomer being ((1S,2S)-2-phenyl-3-aza-bicyclo[3.1.0]hex-1-yl)-carbamic acid tert-butyl ester (0.40 g, 1.5 mmol), diisopropyl ethyl amine (0.25 mL, 1.5 mmol), and acetonitrile (8 mL). The reaction was heated to remove the methylene chloride and then refluxed for 2 hours. The solvent was removed at reduced pressure and the residue was partitioned between saturated citric acid solution and methylene chloride. The organic phase was washed with saturated sodium bicarbonate solution, brine, dried over sodium sulfate, filtered, and concentrated to give the title compounds as a foam (0.84 g, quantitative yield).

후처리

  1. temperatureThe reaction was heated
  2. customto remove the methylene chloride
  3. temperaturerefluxed for 2 hours
  4. customThe solvent was removed at reduced pressure
  5. customthe residue was partitioned between saturated citric acid solution and methylene chloride
  6. washThe organic phase was washed with saturated sodium bicarbonate solution, brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-ee0fdaa97fef495bbf2e93c8464d91bf
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07241798B2

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