Acetic Acid → HCID 178427877, compound

HRID 536663Notes

Reaction equation

HRID 536663 reaction equation
[N:1]([O-])=O.[Na+].[NH2:5][C:6]1[C:27]([NH2:28])=[CH:26][C:9]2[CH2:10][C@@H:11]3[C:16]([CH3:18])([CH3:17])[C@:15]([CH3:19])([C:8]=2[CH:7]=1)[CH2:14][CH2:13][N:12]3[C:20](=[O:25])[C:21]([F:24])([F:23])[F:22].C(O)(=O)C>O>[F:23][C:21]([F:24])([F:22])[C:20]([N:12]1[CH2:13][CH2:14][C@:15]2([CH3:19])[C:16]([CH3:17])([CH3:18])[C@H:11]1[CH2:10][C:9]1[CH:26]=[C:27]3[N:28]=[N:1][NH:5][C:6]3=[CH:7][C:8]=12)=[O:25]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 23668193Sodium NitriteHCID 58123670HCID 58123670, compound

Product 1

HCID 178427877HCID 178427877, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of NaNO2 (330 mg) in water (2 mL) is slowly added to a flask charged with a stir bar, 1-[(2R,6S)-8,9-diamino-6,11,11-trimethyl-1,2,5,6-tetrahydro-4H-2,6-methano-benzo[d]azocin-3-yl]-2,2,2-trifluoro-ethanone (650 mg), and acetic acid (15 mL) and chilled in an ice bath. The resulting mixture is stirred in the cooling bath for 2 h and at ambient temperature for 1 h. Then, the solution is poured into ice-cold water and the precipitate formed is separated by filtration and dried to afford the title compound that is used without further purification.

Workup

  1. additioncharged with a stir bar
  2. additionThen, the solution is poured into ice-cold water
  3. customthe precipitate formed
  4. customis separated by filtration
  5. customdried

Sources & evidence

ORD record
ord-97e3ea0a6df8496eb567ef8fe2874b27
Source dataset
uspto-grants-2014_10
Patent number
US08859580B2

Reaction notes

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