Hydroxylamine → HCID 136355235, compound

HRID 1593491Notes

Reaction equation

HRID 1593491 reaction equation
[CH3:1][N:2]([CH:26]1[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]1)[C:3]([C:5]1[S:6][C:7]([C:16]2[CH:17]=[C:18]3[C:22](=[CH:23][CH:24]=2)[C:21](=O)[CH2:20][CH2:19]3)=[C:8]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[CH:9]=1)=[O:4].[NH2:33][OH:34]>C(O)C>[CH3:1][N:2]([CH:26]1[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]1)[C:3]([C:5]1[S:6][C:7]([C:16]2[CH:17]=[C:18]3[C:22](=[CH:23][CH:24]=2)[C:21](=[N:33][OH:34])[CH2:20][CH2:19]3)=[C:8]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[CH:9]=1)=[O:4]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 69513230HCID 69513230, compound

Product 1

HCID 136355235HCID 136355235, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

The product of step 4 (300 mg, 0.8 mmol) was heated at reflux in ethanol (10 ml) containing hydroxylamine (50% aqueous solution) (1 ml) for 1 hour. The solution was co-evaporated in ethanol (×3) to afford a crude solid. The product was purified twice by silica gel chromatography (1:9:40 0.880 ammonia:thanol:dichloromethane) to afford the title compound (80 mg, 22%); MS (AP+) m/e 461 [M+H]+

Workup

  1. customto afford a crude solid
  2. customThe product was purified twice by silica gel chromatography (1:9:40 0.880 ammonia:thanol:dichloromethane)

Sources & evidence

ORD record
ord-f440e7e39ccf4206a8adf6d4e69bc73a
Source dataset
uspto-grants-2007_11
Patent number
US07297693B2

Reaction notes

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