Hydroxylamine → HCID 46852757, compound

HRID 404171Notes

Reaction equation

HRID 404171 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]=[C:24]([O:26][CH2:27][CH2:28][CH3:29])[CH:23]=[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]=[C:24]([O:26][CH2:27][CH2:28][CH3:29])[CH:23]=[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 58545064HCID 58545064, compound

Product 1

HCID 46852757HCID 46852757, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

HONH2 (50% aqueous, 2 mL) was added to III (16 mg, 0.045 mmol) in DMF (0.5 mL) and MeOH (2 mL) at rt. The reaction mixture was stirred for 22.5 h, after which the solvents were evaporated under reduced pressure. The resulting residue was dissolved and co-evaporated with toluene (2×2 mL) then was purified by silica gel column chromatography eluting with CH2Cl2/MeOH (100:5 to 100:8) to furnish IV as a colourless oil (14 mg, 50%).

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 (100:5 to 100:8)

Sources & evidence

ORD record
ord-9c21261ba04046098e39fe88d3ebbfe3
Source dataset
uspto-grants-2014_06
Patent number
US08748458B2

Reaction notes

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