Triethylamine → HCID 57939120, compound

HRID 1436355Notes

Reaction equation

HRID 1436355 reaction equation
[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].[CH2:6]([C:8]1([CH3:51])[CH:13]([CH3:14])[CH:12]([OH:15])[CH2:11][C:10]([CH2:17][CH3:18])([CH3:16])[N:9]1[O:19][CH:20]([CH3:50])[C:21]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][NH:30][C:31](=[O:49])[CH:32]([O:34][N:35]1[C:40]([CH2:42][CH3:43])([CH3:41])[CH2:39][CH:38]([OH:44])[CH:37]([CH3:45])[C:36]1([CH2:47][CH3:48])[CH3:46])[CH3:33])=[O:22])[CH3:7].C(N([CH2:57][CH3:58])CC)C.[C:59](OCC)(=[O:61])C>>[C:1]([O:15][CH:12]1[CH2:11][C:10]([CH2:17][CH3:18])([CH3:16])[N:9]([O:19][CH:20]([CH3:50])[C:21]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][NH:30][C:31]([CH:32]([O:34][N:35]2[C:40]([CH2:42][CH3:43])([CH3:41])[CH2:39][CH:38]([O:44][C:59](=[O:61])[CH:57]=[CH2:58])[CH:37]([CH3:45])[C:36]2([CH2:47][CH3:48])[CH3:46])[CH3:33])=[O:49])=[O:22])[C:8]([CH2:6][CH3:7])([CH3:51])[CH:13]1[CH3:14])(=[O:4])[CH:2]=[CH2:3]

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 13140Acryloyl chlorideHCID 20826112HCID 20826112, compound

Product 1

HCID 57939120HCID 57939120, compound

Procedure

Acryloylchloride (0.27 g, 3.0 mmol) is added dropwise and below 20° C. to a solution of 0.98 g (1.5 mmol) of 2-(2,6-Diethyl-4-hydroxy-2,3,6-trimethyl-piperidin-1-yloxy)-N-{6-[2-(2,6-diethyl-4-hydroxy-2,3,6-trimethyl-piperidin-1-yloxy)-propionylamino]-hexyl}-propionamide (prepared as described in WO 03/004471 A1, example A3) and 0.3 g (3.0 mmol) triethylamine in 30 ml ethyl acetate. The mixture is stirred for 12 h at room temperature, then washed with 3×10 ml water, dried over Na2SO4 and evaporated. Chromatography of the residue over silica gel with hexane-ethyl acetate (3:2) afford 0.33 g of the title compound as a viscous slightly yellow oil.

Workup

  1. washwashed with 3×10 ml water
  2. dry with materialdried over Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-09190b6730994f03a68fed0c71b28e73
Source dataset
uspto-grants-2009_11
Patent number
US07619050B2

Reaction notes

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