O-(Diphenylphosphinyl)hydroxylamine → HCID 67160981, compound

HRID 469523Notes

Reaction equation

HRID 469523 reaction equation
[CH:1]([C:4]1[C:13]2[CH:12]3[CH2:14][CH2:15][CH:9]([CH2:10][CH2:11]3)[C:8]=2[C:7](=[O:16])[NH:6][N:5]=1)([CH3:3])[CH3:2].CC([O-])(C)C.[K+].C1(P(O[NH2:38])(C2C=CC=CC=2)=O)C=CC=CC=1>C1COCC1.CN(C=O)C.CCOC(C)=O>[NH2:38][N:6]1[N:5]=[C:4]([CH:1]([CH3:3])[CH3:2])[C:13]2[CH:12]3[CH2:14][CH2:15][CH:9]([CH2:10][CH2:11]3)[C:8]=2[C:7]1=[O:16]

Participants

7

Reactant 3

HCID 10955453O-(Diphenylphosphinyl)hydroxylamineHCID 23665647Potassium tert-butoxideHCID 67160996HCID 67160996, compound

Product 1

HCID 67160981HCID 67160981, compoundYield 54.5%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of Example 8B (31.5 mg, 0.144 mmol) and KOtBu (1 M in THF, 0.16 mL, 0.16 mmol) in THF (0.3 mL) and DMF (0.2 mL) was stirred for 30 minutes, and O-(diphenylphosphoryl)hydroxylamine (37.0 mg, 0.159 mmol) was added and stirred 4 h. The mixture was diluted with EtOAc, washed with saturated aqueous NaHCO3 and brine, dried (Na2SO4), and filtered. The residue was chromatographed on SiO2 (2.5% MeOH/CH2Cl2) to give the title compound as a white solid (18.3 mg) which was used without further purification. LC/MS (APCI) M/Z 234.2 (M+H)+.

Workup

  1. washwashed with saturated aqueous NaHCO3 and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customThe residue was chromatographed on SiO2 (2.5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-065f5911f925417abbed238400d260e2
Source dataset
uspto-grants-2014_01
Patent number
US08629143B2

Reaction notes

Loading…