Hydroxylamine → 7-[(4-Benzyloxy-pyridin-2-yl)-pyridin-2-yl-amino]-heptanoic acid hydroxyamide

HRID 523921Notes

Reaction equation

HRID 523921 reaction equation
[OH:1][NH2:2].C(O[C:6](=[O:34])[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][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[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:34])[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][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[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 866601447-[(4-Benzyloxy-pyridin-2-yl)-pyridin-2-yl-amino]heptanoic acid ethyl ester

Product 1

HCID 468526117-[(4-Benzyloxy-pyridin-2-yl)-pyridin-2-yl-amino]-heptanoic acid hydroxyamideYield 41%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

HONH2 (50% aqueous, 1 mL) was added to III (47 mg, 0.11 mmol) in DMF (0.2 mL) and MeOH (0.5 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 (2×2 mL) then was purified by silica gel column chromatography eluting with CH2Cl2/MeOH (100:5) to furnish IV as a colourless oil (19 mg, 41%).

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)

Sources & evidence

ORD record
ord-9a24f14eb72440fb97e0e0d2bc5bcf90
Source dataset
uspto-grants-2016_05
Patent number
US09340503B2

Reaction notes

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