Methanol → HCID 137231142, compound

HRID 2276047Notes

Reaction equation

HRID 2276047 reaction equation
[CH:1]([C:3]1[N:8]=[C:7]2[CH2:9][O:10][C:11]3([CH2:14][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:12]3)[C:6]2=[CH:5][CH:4]=1)=O.CO.CC([O-])=O.[Na+].[NH2:29][OH:30].Cl>O>[OH:30][N:29]=[CH:1][C:3]1[N:8]=[C:7]2[CH2:9][O:10][C:11]3([CH2:14][N:13]([C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])[CH2:12]3)[C:6]2=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 89996173HCID 89996173, compound

Product 1

HCID 137231142HCID 137231142, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of tert-butyl 2′-formyl-7′H-spiro[azetidine-3,5′-furo[3,4-b]pyridine]-1-carboxylate (0.5 g, 1.7 mmol, 1 eq.) in mixture of methanol (12 mL):water (12 mL) was added NaOAc (0.28 g, 3.45 mmol, 2 eq.) followed by addition of NH2OH.HCl (0.24 g, 3.45 mmol, 2 eq.) at room temperature. Resulting reaction mixture was stirred at room temperature for 18 hours under nitrogen atmosphere. After complete consumption starting material, reaction mixture was concentrated under reduced pressure; resulting residue was diluted with water (50 mL) and extracted by ethyl acetate (3×100 mL). Combined organic layer was dried over sodium sulphate and concentrated under reduced pressure to afford title compound as brown solid (0.520 g, 99%). 1H NMR (400 MHz, CDCl3) δ: 1.47 (s, 9H), 4.12 (d, J=9.88 Hz, 2H), 4.34 (d, J=10.12 Hz, 2H), 5.08 (s, 2H), 7.73 (d, J=7.92 Hz, 1H), 7.79 (d, J=7.96 Hz, 1H), 8.21 (s, 1H). LC-MS (m/z): 306.3 (M+H).

Workup

  1. customResulting
  2. customreaction mixture
  3. customAfter complete consumption
  4. custommaterial, reaction mixture
  5. concentrationwas concentrated under reduced pressure
  6. additionresulting residue was diluted with water (50 mL)
  7. extractionextracted by ethyl acetate (3×100 mL)
  8. dry with materialCombined organic layer was dried over sodium sulphate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1cae7fb3c95444e7953e9fb62a6aace1
Source dataset
uspto-grants-2015_09
Patent number
US09131697B2

Reaction notes

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