Methanol → HCID 68922254, compound

HRID 1788517Notes

Reaction equation

HRID 1788517 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[C:5]1[CH:10]=[CH:9][C:8](Cl)=[C:7]([N+:12]([O-:14])=[O:13])[CH:6]=1)[CH3:2].C(N(CC)CC)C.Cl.[NH2:24][C@@H:25]1[CH2:30][CH2:29][CH2:28][CH2:27][C@H:26]1[OH:31].CO>C(#N)C.O>[CH2:1]([O:3][C:4](=[O:15])[C:5]1[CH:10]=[CH:9][C:8]([NH:24][C@@H:25]2[CH2:30][CH2:29][CH2:28][CH2:27][C@H:26]2[OH:31])=[C:7]([N+:12]([O-:14])=[O:13])[CH:6]=1)[CH3:2]

Participants

7

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 1268247Ethyl 4-chloro-3-nitrobenzoateHCID 12228412Cyclohexanol, 2-amino-, hydrochloride (1:1), (1R,2R)-

Product 1

HCID 68922254HCID 68922254, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Compound 9 (689 mg, 3 mmol) was suspended in acetonitrile (5 mL) and then triethylamine was added (1.3 mL, 9 mmol). trans-2-aminocyclohexanol hydrochloride (682 mg, 4.5 mmol) was then added and the reaction refluxed for 12 hours, 2 mL methanol was then added and the reaction further refluxed for another 24 hours. Water (100 mL) was added and the resulting precipitate filtered, washed 3 times with water and air-dried. The product was used without further characterization in the next step. MS: 309.3 (M+H+)

Workup

  1. temperaturethe reaction refluxed for 12 hours
  2. customthe reaction
  3. temperaturefurther refluxed for another 24 hours
  4. filtrationthe resulting precipitate filtered
  5. washwashed 3 times with water
  6. customair-dried

Sources & evidence

ORD record
ord-38b97266a3fd4f0495c8c608fcb0193f
Source dataset
uspto-grants-2009_03
Patent number
US07511145B2

Reaction notes

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