Triethylamine → HCID 178470806, compound

HRID 1798282Notes

Reaction equation

HRID 1798282 reaction equation
[C:1]([C:3]1[S:7][C:6]([O:8][C:9]2[CH:10]=[C:11]([CH3:25])[C:12]3[CH:16]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[O:15][B:14]([OH:23])[C:13]=3[CH:24]=2)=[N:5][CH:4]=1)#[N:2].Cl.[NH2:27][OH:28].C(N(CC)CC)C>CO>[OH:23][B:14]1[C:13]2[CH:24]=[C:9]([O:8][C:6]3[S:7][C:3]([C:1](=[NH:2])[NH:27][OH:28])=[CH:4][N:5]=3)[CH:10]=[C:11]([CH3:25])[C:12]=2[CH:16]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[O:15]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 67253421Ethyl 2-(6-(5-cyanothiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate

Product 1

HCID 178470806HCID 178470806, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 2-(6-(5-cyanothiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (2.5 g, 7 mmol, 1 eq.) and hydroxylamine hydrochloride (1.21 g, 17.4 mmol, 2.5 eq.) in methanol was added triethylamine (3.41 ml, 24.5 mmol, 3.5 eq.). After stirring at room temperature overnight, 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 yellow solid. 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-aacbc887e96e4e7aa383ba2198b95a78
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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