N,O-Dimethylhydroxylamine → HCID 19967216, compound

HRID 976450Notes

Reaction equation

HRID 976450 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1CC(O)C(O)=O.[O:16]([Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])S(C(F)(F)F)(=O)=O.ClC([O:34][CH2:35][CH:36]([CH3:38])C)=O.[CH3:39][NH:40][O:41][CH3:42]>ClCCl.C(N(CC)CC)C>[CH3:42][O:41][N:40]([CH3:39])[C:35](=[O:34])[CH:36]([O:16][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[CH2:38][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1

Participants

7

Reactant 4

HCID 14232N,O-DimethylhydroxylamineHCID 62365Isobutyl chloroformateHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 53700591HCID 53700591, compound

Product 1

HCID 19967216HCID 19967216, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent2×

Procedure

Indole lactic acid (5.0 g) was suspended in dichloromethane (100 ml) and treated with triethylamine (6.8 ml) and t-butyldimethylsilyl triflate (5.7 ml) for 24 hours. iso-Butyl chloroformate (3.1 ml) was added followed by N,O-dimethylhydroxylamine (2.4 g) and triethylamine (3.4 ml). The solution was stirred for 24 hours then washed with water, dried (Na2SO4) and concentrated. The residue was purified by chromatography on silica gel eluting with ethyl acetate-petroleum ether to give the title compound as a white solid.

Workup

  1. washthen washed with water
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was purified by chromatography on silica gel eluting with ethyl acetate-petroleum ether

Sources & evidence

ORD record
ord-916e23029c3c40bfb0bff4baccd927df
Source dataset
uspto-grants-1997_03
Patent number
US05612362

Reaction notes

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