hydroxylamine-O-sulfonic acid → Hexahydro-b-(4-methylphenyl)-2-oxo-1h-azepine-3-propanoic acid

HRID 849141Notes

Reaction equation

HRID 849141 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[CH:8]([C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)[CH2:9][C:10]([OH:12])=[O:11].[NH2:20]OS(O)(=O)=O>C(O)=O>[CH3:19][C:16]1[CH:17]=[CH:18][C:13]([CH:8]([CH:3]2[CH2:4][CH2:5][CH2:6][CH2:7][NH:20][C:2]2=[O:1])[CH2:9][C:10]([OH:12])=[O:11])=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 76284hydroxylamine-O-sulfonic acidHCID 18800826beta-(2-Oxocyclohexyl)-4-methylbenzenepropanoic acid

Product 1

HCID 18800654Hexahydro-b-(4-methylphenyl)-2-oxo-1h-azepine-3-propanoic acid

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent2×

Procedure

The title material of Example 201 in formic acid is added to a solution of hydroxylamine-O-sulfonic acid in formic acid over a 5 min. period with stirring under N2. The mixture is heated under reflux for 3 hours and then cooled to room temperature. The reaction is quenched with cold water and the solution is neutralized with 6N NaOH. It is then extracted three times with CH2Cl2. The combined organic layers are dried over MgSO4 and the solvent is removed on a rotary evaporator. The desired products are purified and isolated by HPLC to give both the 3- and 7-substituted title products.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 3 hours
  3. customThe reaction is quenched with cold water
  4. extractionIt is then extracted three times with CH2Cl2
  5. dry with materialThe combined organic layers are dried over MgSO4
  6. customthe solvent is removed on a rotary evaporator
  7. customThe desired products are purified
  8. customisolated by HPLC
  9. customto give both the 3- and 7-substituted title products

Sources & evidence

ORD record
ord-b59c93c2adc946e8b3e24853d908d695
Source dataset
uspto-grants-2000_01
Patent number
US06011028

Reaction notes

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