Triethylamine → HCID 178470804, compound

HRID 1798190Notes

Reaction equation

HRID 1798190 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]([O:9][C:10]2[CH:11]=[C:12]([CH3:26])[C:13]3[CH:17]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[O:16][B:15]([OH:24])[C:14]=3[CH:25]=2)[CH:4]=1)#[N:2].Cl.[NH2:28][OH:29].C(N(CC)CC)C>>[OH:24][B:15]1[C:14]2[CH:25]=[C:10]([O:9][C:5]3[CH:4]=[C:3]([C:1](=[NH:2])[NH:28][OH:29])[CH:8]=[CH:7][N:6]=3)[CH:11]=[C:12]([CH3:26])[C:13]=2[CH:17]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[O:16]1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 67253702Ethyl 2-(6-(4-cyanopyridin-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate

Product 1

HCID 178470804HCID 178470804, compoundYield 95%

Procedure

To a solution of ethyl 2-(6-(4-cyanopyridin-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (0.8 g, 2.27 mmol, 1 eq.) and hydroxylamine hydrochloride (0.4 g, 5.68 mmol, 2.5 eq.) in methanl was added triethylamine (1.11 ml, 7.95 mmol, 3.5 eq.). After stirring at room temperature overnight, the starting material was gone but no right mass was observed. The reaction mixture was evaporated under reduced pressure. The residue was dissolved in EtOAc and then washed with water. The organic layers were collected, dried with Na2SO4 and evaporated to give the crude product as a colorless oil (0.83 g, yield 95%). The crude was used in subsequent steps without further purification.

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with water
  4. customThe organic layers were collected
  5. dry with materialdried with Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-1d72d212b8424677b8e413038568d5f0
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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