Nitric Acid → HCID 89419880, compound

HRID 920178Notes

Reaction equation

HRID 920178 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@@:8]1([CH3:20])[N:16]=[C:15]([NH2:17])[C:11]2([CH2:14][CH2:13][CH2:12]2)[S:10](=[O:19])(=[O:18])[CH2:9]1.S(=O)(=O)(O)O.[N+:26]([O-])([OH:28])=[O:27].[OH-].[Na+]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:26]([O-:28])=[O:27])=[CH:4][C:3]=1[C@@:8]1([CH3:20])[N:16]=[C:15]([NH2:17])[C:11]2([CH2:12][CH2:13][CH2:14]2)[S:10](=[O:19])(=[O:18])[CH2:9]1

Participants

5

Reactant 4

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 90024450HCID 90024450, compound

Product 1

HCID 89419880HCID 89419880, compoundYield 106.2%

Conditions

Temperature
0 °C

Procedure

(R)-7-(2-Fluoro-phenyl)-7-methyl-5,5-dioxo-5λ6-thia-8-aza-spiro[3.5]non-8-en-9-ylamine (385 mg, 1.3 mmol, Eq: 1.00) was dissolved in conc. sulfuric acid (6.37 g, 3.46 ml, 65.0 mmol, Eq: 50). At 0° C., fuming nitric acid (123 mg, 87.1 μl, 1.95 mmol, Eq: 1.5) was added dropwise. The light brown solution was stirred at 0° C. for 2 hours. The reaction mixture was poured on ice and basified with 3 N NaOH followed by extraction with dichloromethane. The organic layer was separated, dried over Na2SO4, filtered and evaporated to dryness to give the crude and pure (R)-7-(2-fluoro-5-nitro-phenyl)-7-methyl-5,5-dioxo-5λ6-thia-8-aza-spiro[3.5]non-8-en-9-ylamine (470 mg, 1.38 mmol, 106% yield) as a light brown foam. MS (ISP): m/z=342.1 [M+H]+.

Workup

  1. extractionfollowed by extraction with dichloromethane
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-807ef24c5c9940c8b8bde4ae658d619c
Source dataset
uspto-grants-2016_03
Patent number
US09273042B2

Reaction notes

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