Water → HCID 86722642, compound

HRID 1480403Notes

Reaction equation

HRID 1480403 reaction equation
[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)=[N+:2]=[N-:3].[C:13]([OH:21])(=[O:20])[CH2:14][CH2:15][CH2:16][CH2:17][C:18]#[CH:19].O.O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+].[Cl-].[Na+]>CC(O)(C)C.CCOC(C)=O>[CH3:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([CH2:4][N:1]2[CH:19]=[C:18]([CH2:17][CH2:16][CH2:15][CH2:14][C:13]([OH:21])=[O:20])[N:3]=[N:2]2)=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 962WaterHCID 5234Sodium ChlorideHCID 43779506-Heptynoic acidHCID 109317671-(Azidomethyl)-4-methoxybenzeneHCID 23667548Sodium Ascorbate

Product 1

HCID 86722642HCID 86722642, compound

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(Azidomethyl)-4-methoxybenzene (259 mg, 1.585 mmol) was solubilised in t-BuOH (15.9 ml). Hept-6-ynoic acid (201 μl, 1.585 mmol) was added followed by water (15.9 ml) copper acetate (28.2 mg, 0.159 mmol) and sodium L-ascorbate (63 mg, 0.317 mmol). The reaction mixture was stirred at RT for 72 hrs. Sodium chloride was added and the mixture was stirred vigorously. EtOAc was added and the phases were separated. The aqueous layer was re-extracted with EtOAc and the combined organics were treated with charcoal & MgSO4 (anh), stirring for 5 minutes. The resulting mixture was filtered and the filtrate was evaporated under reduced pressure to afford the title compound;

Workup

  1. stirringthe mixture was stirred vigorously
  2. customthe phases were separated
  3. extractionThe aqueous layer was re-extracted with EtOAc
  4. additionthe combined organics were treated with charcoal & MgSO4 (anh)
  5. stirringstirring for 5 minutes
  6. filtrationThe resulting mixture was filtered
  7. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-6ccff296d367485ab0d4bd78ff35e1b2
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

Loading…