Hydroxylamine → HCID 86744228, compound

HRID 1032564Notes

Reaction equation

HRID 1032564 reaction equation
N[OH:2].C([N:5]([CH2:8][CH3:9])[CH2:6][CH3:7])C.C(Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13]C=1.[C:18](=[O:21])([O-])[O-].[K+].[K+].[CH2:24]([O:31][C:32](Cl)=[O:33])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[CH2:35]1[CH2:39]O[CH2:37][CH2:36]1>C(Cl)(Cl)Cl.O>[C:25]1([CH2:24][O:31][C:32]([N:5]([C:6]23[O:2][CH:35]([CH2:39][CH2:7]2)[CH2:36][CH:37]3[CH2:18][OH:21])[CH2:8][C:9]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:11]=2)=[O:33])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

9

Reactant 6

HCID 787HydroxylamineHCID 7498Benzyl BromideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 11430Potassium Carbonate

Product 1

HCID 86744228HCID 86744228, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6212ChloroformSolvent

Conditions

Temperature
2.5 °C

Procedure

To a solution of 1.6 gm (0.01 mole) of Example 8 amino alcohol in 20 ml chloroform is added triethylamine (1.1 gm, 0.011 mole) followed by benzylbromide (1.7 gm, 0.01 mole). The mixture is refluxed for 10 hours where upon TLC indicates the absence of any starting material. The residue obtained on removal of the solvent is dissolved in 10 ml THF and 10 ml water and 1.4 gms of potassium carbonate is added to it and the mixture cooled in an ice bath to 0-5° C. Benzyloxycarbonyl chloride (Z-Cl), (2 gm, 0.011 mole) is added to it and the mixture stirred at 0-5° C. for 2 hours. It is diluted with water and extracted with ethyl acetate. The crude material obtained on evaporation of the solvent is chromatographed using silica gel and ethyl-acetate hexane solvent (1:1) system to produce title compound.

Workup

  1. temperatureThe mixture is refluxed for 10 hours where upon TLC
  2. customThe residue obtained on removal of the solvent
  3. extractionextracted with ethyl acetate
  4. customThe crude material obtained on evaporation of the solvent
  5. customis chromatographed

Sources & evidence

ORD record
ord-1cb76da29c184e9f8c56e4bd5d2e8f0e
Source dataset
uspto-grants-1990_09
Patent number
US04958036

Reaction notes

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