Acetic Acid → HCID 178432040, compound

HRID 536655Notes

Reaction equation

HRID 536655 reaction equation
[NH2:1][C:2]1[C:23]([NH2:24])=[CH:22][C:5]2[CH2:6][C@@H:7]3[C:12]([CH3:14])([CH3:13])[C@:11]([CH3:15])([C:4]=2[CH:3]=1)[CH2:10][CH2:9][N:8]3[C:16](=[O:21])[C:17]([F:20])([F:19])[F:18].[C:25](O)(=O)[CH3:26]>>[F:19][C:17]([F:20])([F:18])[C:16]([N:8]1[CH2:9][CH2:10][C@:11]2([CH3:15])[C:12]([CH3:13])([CH3:14])[C@H:7]1[CH2:6][C:5]1[CH:22]=[C:23]3[N:24]=[C:25]([CH3:26])[NH:1][C:2]3=[CH:3][C:4]=12)=[O:21]

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 58123670HCID 58123670, compound

Product 1

HCID 178432040HCID 178432040, compound

Conditions

Temperature
130 °C

Procedure

(2R,6S)-1-(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 (600 mg) dissolved in glacial acetic acid is stirred at 130° C. for 3 h. After cooling to ambient temperature, the solution is concentrated under reduced pressure and the residue is taken up in ethyl acetate. The organic solution is washed with aqueous K2CO3 solution and brine and dried (MgSO4). The solvent is removed under reduced pressure to give the crude title compound as a foam-like solid.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. concentrationthe solution is concentrated under reduced pressure
  3. washThe organic solution is washed with aqueous K2CO3 solution and brine
  4. dry with materialdried (MgSO4)
  5. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-e4e617902bff4f4eb36c36f505a3ad2a
Source dataset
uspto-grants-2014_10
Patent number
US08859580B2

Reaction notes

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