Potassium Hydroxide → tert-Butyl 4-(1-oxido-5,6,7,8-tetrahydronaphtho[2,3-c][1,2,5]oxadiazol-6-yl)piperazine-1-carboxylate

HRID 1519512Notes

Reaction equation

HRID 1519512 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([N:12]3[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]3)[CH2:9]2)=[CH:4][C:3]=1[N+:25]([O-:27])=[O:26].[OH-].[K+].Cl[O-].[Na+]>C(O)C>[O-:26][N+:25]1[O:27][N:1]=[C:2]2[CH:11]=[C:10]3[C:5]([CH2:6][CH2:7][CH:8]([N:12]4[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])[CH2:14][CH2:13]4)[CH2:9]3)=[CH:4][C:3]=12

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 23665760Sodium Hypochlorite2×HCID 86694446tert-Butyl 4-(7-amino-6-nitro-1,2,3,4-tetrahydronaphthalen-2-yl)piperazine-1-carboxylate

Product 1

HCID 86694447tert-Butyl 4-(1-oxido-5,6,7,8-tetrahydronaphtho[2,3-c][1,2,5]oxadiazol-6-yl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of tert-Butyl 4-(7-amino-6-nitro-1,2,3,4-tetrahydronaphthalen-2-yl)piperazine-1-carboxylate (160 mg, 0.42 mmol) in ethanol (3 mL) was added potassium hydroxide (36 mg, 0.64 mmol). The solution was stirred until all solids dissolved. At that point, sodium hypochlorite (1.3 mL, 1.3 mmol) was dropped into the reaction. LC showed quite slow reaction. Another 1.3 mL of sodium hypochlorite was added to complete the reaction. The desired product was separated by reverse phase HPLC (water: Acetonitrile with 0.1% TFA). LC-MS (IE, m/z): 375 [M+1]+.

Workup

  1. dissolutiondissolved
  2. customreaction
  3. customthe reaction
  4. customThe desired product was separated by reverse phase HPLC (water: Acetonitrile with 0.1% TFA)

Sources & evidence

ORD record
ord-dd7412ee1b814dd1bb64dcd0d70d0f03
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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