Diisopropylethylamine → HCID 67995869, compound

HRID 1615112Notes

Reaction equation

HRID 1615112 reaction equation
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[Br:13][C:14]1[CH:19]=[CH:18][C:17]([C@@H:20]([NH:22][CH2:23][CH2:24][C:25]([OH:32])([CH2:29][CH:30]=[CH2:31])[CH2:26][CH:27]=[CH2:28])[CH3:21])=[CH:16][CH:15]=1.C(N(C(C)C)C(C)C)C>ClCCl>[CH2:29]([C:25]1([CH2:26][CH:27]=[CH2:28])[O:32][C:2](=[O:4])[N:22]([C@H:20]([C:17]2[CH:16]=[CH:15][C:14]([Br:13])=[CH:19][CH:18]=2)[CH3:21])[CH2:23][CH2:24]1)[CH:30]=[CH2:31]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 67995893HCID 67995893, compound

Product 1

HCID 67995869HCID 67995869, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triphosgene (6.90 g) is added to a solution of 4-{2-[(S)-1-(4-bromo-phenyl)-ethylamino]-ethyl}-hepta-1,6-dien-4-ol (7.86 g) and ethyl-diisopropyl-amine (4 mL) in dichloromethane (150 mL) chilled in an ice bath. The cooling bath is removed and the solution is stirred at room temperature overnight. Water is added and the organic phase is then separated. The organic phase is dried (Na2SO4) and concentrated to give the crude title compound that is used without further purification. Yield: 8.65 g (ca. 90% pure); LC (method 1): tR=4.03 min; Mass spectrum (ESI+): m/z=364/366 (Br) [M+H]+.

Workup

  1. temperaturechilled in an ice bath
  2. customThe cooling bath is removed
  3. additionWater is added
  4. customthe organic phase is then separated
  5. dry with materialThe organic phase is dried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d0870a654c7e4a3780bead930d1ae37c
Source dataset
uspto-grants-2014_07
Patent number
US08765744B2

Reaction notes

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