Triethylamine → HCID 59200464, 화합물

HRID 1685328노트

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HRID 1685328 반응식
[NH2:1][CH2:2][C:3]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:4][OH:5].C(N(CC)CC)C.Cl[C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27]>ClCCl.O>[OH:5][CH2:4][C:3]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:2][NH:1][C:26](=[O:27])[O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 18626554HCID 18626554, 화합물

생성물 1

HCID 59200464HCID 59200464, 화합물수율 47.5%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

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온도
23 °C

실험 절차

A solution of 3-amino-2,2-diphenylpropan-1-ol (18.4 g, 80.95 mmol) in dichloromethane (250 mL) was treated with triethylamine (16.9 mL, 121.4 mmol) and benzyl chloroformate (12.7 mL, 89.0 mmol) was then added dropwise over a period of 15 minutes. The reaction was stirred at 23° C., then diluted with water and stirred for 15 more minutes. The phases were separated and the organic phase was washed with 1N HCl, dried over anhydrous magnesium sulfate, filtered and concentrated to give the crude title material as an oil. This was purified on silica gel column (20% ethyl acetate/hexane) to give the title material (13.9 g, 47%) as an oil. 1H NMR (400 MHz, CDCl3) δ ppm: 2.29 (1H, br s), 4.08 (2H, d, J=6.57 Hz), 4.20 (2H, s), 4.82 (1H, t, J=6.06 Hz), 5.12 (2H, s), 7.14-7.21 (4H, m), 7.23-7.29 (2H, m), 7.31-7.41 (9H, M). HPLC ret. time (Condition C): 6.098 min. LC/MS (M+H)+: 362.

후처리

  1. additionwas then added dropwise over a period of 15 minutes
  2. stirringstirred for 15 more minutes
  3. customThe phases were separated
  4. washthe organic phase was washed with 1N HCl
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give the crude title material as an oil
  9. customThis was purified on silica gel column (20% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-17446026856a4842bb08cfad4d6fda90
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148400B2

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