Triethylamine → HCID 59525960, compound

HRID 385765Notes

Reaction equation

HRID 385765 reaction equation
[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]([CH2:7][NH:8][C@@H:9]([CH3:12])[CH2:10][OH:11])=[CH:5][CH:4]=1.C(N(CC)CC)C.[Br:22][CH2:23][C:24](Br)=[O:25]>ClCCl>[Br:22][CH2:23][C:24]([N:8]([C@@H:9]([CH3:12])[CH2:10][OH:11])[CH2:7][C:6]1[CH:13]=[CH:14][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[O:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61147Bromoacetyl bromideHCID 60073977HCID 60073977, compound

Product 1

HCID 59525960HCID 59525960, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-21 °C

Procedure

Into a 20000 mL 4-necked, round bottomed flask purged and maintained with an inert atmosphere of nitrogen was placed a solution of (S)-2-(4-methoxybenzylamino)propan-1-ol (300 g, 1.54 mol) in dichloromethane (12000 mL) and triethylamine (155.8 g, 1.54 mol). 2-Bromoacetyl bromide (310.8 g, 1.54 mol) was added dropwise, while cooling to a temperature of −17 to −25° C. and maintained at this temperature for 4 hours. The reaction mixture was warmed to room temperature and washed three times with 2000 mL of water, dried over MgSO4, filtered, and concentrated under vacuum to afford the title compound as a yellow oil.

Workup

  1. customInto a 20000 mL 4-necked, round bottomed flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. temperaturemaintained at this temperature for 4 hours
  4. temperatureThe reaction mixture was warmed to room temperature
  5. washwashed three times with 2000 mL of water
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-00191bb27f1a4a4392f1b96991838e00
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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