Lithium Hydroxide → HCID 135915155, compound

HRID 447711Notes

Reaction equation

HRID 447711 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH3:12])[CH:10]=2)[NH:5][C:4](=[S:13])[C:3]=1[C:14]([C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1)=O.[NH2:23]OS(O)(=O)=O.[OH-].[Li+]>CO>[CH3:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[NH:5][C:4]1[S:13][N:23]=[C:14]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=3)[C:3]=1[C:2]2=[O:1]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 76284hydroxylamine-O-sulfonic acidHCID 136342249HCID 136342249, compound

Product 1

HCID 135915155HCID 135915155, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 13 (80 mg, 0.259 mmol) in 25 mL of methanol was added a solution of hydroxylamine-O-sulfonic acid (102.6 mg, 0.907 mol) and lithium hydroxide (38.1 mg, 0.907 mmol) in 3 mL of methanol and the mixture was stirred at room temperature for 30 hours. The reaction mixture was concentrated under reduced pressure and applied to flash chromatography. Elution with heptane/EtOAc (3:1) gave 19 as a white solid (44 mg, 55%). mp: 330° C.;

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. washElution with heptane/EtOAc (3:1)

Sources & evidence

ORD record
ord-a63960409c3e499198bc2d9c76c0fb7d
Source dataset
uspto-grants-2013_07
Patent number
US08481561B2

Reaction notes

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