Triethylamine → HCID 59200464, compound

HRID 1685328Notes

Reaction equation

HRID 1685328 reaction equation
[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

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 18626554HCID 18626554, compound

Product 1

HCID 59200464HCID 59200464, compoundYield 47.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-17446026856a4842bb08cfad4d6fda90
Source dataset
uspto-grants-2012_04
Patent number
US08148400B2

Reaction notes

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