Hydroxylamine → HCID 46852608, compound

HRID 404158Notes

Reaction equation

HRID 404158 reaction equation
[OH:1][NH2:2].C([O:5][C:6](=O)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]([C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:22][N:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)C>CN(C=O)C.CO>[OH:1][NH:2][C:6](=[O:5])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]([C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[CH:22][N:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1

Participants

5

Reactant 2

HCID 787HydroxylamineHCID 58545061HCID 58545061, compound

Product 1

HCID 46852608HCID 46852608, compoundYield 7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

HONH2 (50% aqueous, 2 mL) was added the crude batch of III (16 mg) in DMF (0.5 mL) and MeOH (2 mL) at rt. The reaction mixture was stirred for 72 h, after which the solvents were evaporated under reduced pressure. The resulting residue was dissolved and co-evaporated with toluene (2×3 mL) then was purified by silica gel column chromatography eluting with CH2Cl2/MeOH (100:8 then 100:10) to furnish IV as a colourless oil (1.36 mg, 7% over two steps).

Workup

  1. customafter which the solvents were evaporated under reduced pressure
  2. dissolutionThe resulting residue was dissolved
  3. customthen was purified by silica gel column chromatography
  4. washeluting with CH2Cl2/MeOH (100:8

Sources & evidence

ORD record
ord-a861d0331d124640a90173b93c8eb62a
Source dataset
uspto-grants-2014_06
Patent number
US08748458B2

Reaction notes

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