Hydroxyamine hydrochloride → HCID 73988975, compound

HRID 2181276Notes

Reaction equation

HRID 2181276 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1([S:23]([C:26]2[CH:31]=[CH:30][C:29]([CH:32]=O)=[CH:28][CH:27]=2)(=[O:25])=[O:24])[CH2:14][CH2:13][CH:12]([NH:15][S:16]([C:19]([F:22])([F:21])[F:20])(=[O:18])=[O:17])[CH2:11][CH2:10]1.Cl.[NH2:35][OH:36].C([O-])(=O)C.[Na+]>C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1([S:23]([C:26]2[CH:31]=[CH:30][C:29]([CH:32]=[N:35][OH:36])=[CH:28][CH:27]=2)(=[O:25])=[O:24])[CH2:14][CH2:13][CH:12]([NH:15][S:16]([C:19]([F:22])([F:21])[F:20])(=[O:18])=[O:17])[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 20781254HCID 20781254, compound

Product 1

HCID 73988975HCID 73988975, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the product of Example 80 (0.40 g, 0.80 mmol), hydroxylamine hydrochloride (0.16 g, 2.4 mmol) and sodium acetate (0.19 g, 2.4 mmol) in ethanol (60 ml) was heated at reflux for 16 hours and stirred at room temperature for 32 hours. The mixture was evaporated in vacuo and extracted with ethyl acetate (50 ml). The organic phase was washed with brine (sat. 40 ml), dried (magnesium sulfate) and evaporated in vacuo. The crude product was chromatographed on silica, eluting with 20-28% ethyl acetate/isohexane to give the oxime (0.36 g, 87%). 1H NMR (DMSO, 360 MHz): 1.49 (2H, bt, J=12.3), 1.82 (2H, bd, J=14.0), 2.40 (2H, bt, J=13.8), 2.50-2.60 (2H, m), 3.64 (1H, bs), 7.08-7.20 (2H, m), 7.28-7.34 (1H, m), 7.37 (2H, d, J=8.3), 7.72 (2H, d, J=8.3), 8.24 (1H, s), 9.76 (0.5H, d, J=5.9), 11.74 (0.5H, s)

Workup

  1. temperatureat reflux for 16 hours
  2. customThe mixture was evaporated in vacuo
  3. extractionextracted with ethyl acetate (50 ml)
  4. washThe organic phase was washed with brine (sat. 40 ml)
  5. dry with materialdried (magnesium sulfate)
  6. customevaporated in vacuo
  7. customThe crude product was chromatographed on silica
  8. washeluting with 20-28% ethyl acetate/isohexane

Sources & evidence

ORD record
ord-729c667db3814a04b0912cdfc1303943
Source dataset
uspto-grants-2005_05
Patent number
US06890956B2

Reaction notes

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