Triethylamine → HCID 86628980, compound

HRID 748164Notes

Reaction equation

HRID 748164 reaction equation
[C:1]([O:10]C)(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[SH:4].C(C1C(CCCOCCC(OC(C)(C)C)=O)=CC=CN=1)#N.[C:33]([C:35]1[CH:40]=[CH:39][C:38]([CH2:41][CH2:42][CH2:43][O:44][CH2:45][CH2:46][C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])=[CH:37][N:36]=1)#[N:34].C(N(CC)CC)C>C1(C)C=CC=CC=1>[O:10]=[C:1]1[C:2]2[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=2[S:4][C:33]([C:35]2[N:36]=[CH:37][C:38]([CH2:41][CH2:42][CH2:43][O:44][CH2:45][CH2:46][C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])=[CH:39][CH:40]=2)=[N:34]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 68455132HCID 68455132, compoundHCID 68456385HCID 68456385, compound

Product 1

HCID 86628980HCID 86628980, compoundYield 16.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of methyl thiosalicylate (2.80 g, 16.6 mmol), a mixture of tert-butyl 3-[(2-cyanopyridin-3-yl)propoxy]propionate and tert-butyl 3-[(2-cyanopyridin-5-yl)propoxy]propionate (ca. 9:1, 4.55 g, 15.7 mmol), triethylamine (2.02 g, 20 mmol) and toluene (20 ml) was refluxed under nitrogen atmosphere for 20 hrs. The reaction mixture was concentrated under reduced pressure. The residue was subjected to a silica gel column chromatography, eluted with ethyl acetate-hexane (2:1, v/v) to give the titled compound (1.10 g, 16%).

Workup

  1. temperaturewas refluxed under nitrogen atmosphere for 20 hrs
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. washeluted with ethyl acetate-hexane (2:1

Sources & evidence

ORD record
ord-5fa98b184dee468e9b5defb54afece9f
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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