Hydrochloric Acid → HCID 12160907, compound

HRID 1480472Notes

Reaction equation

HRID 1480472 reaction equation
[CH2:1]([NH:4]C(=O)OC(C)(C)C)[C:2]#[CH:3].[N:12]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[N+:13]=[N-:14].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+].Cl.[Na+].[Cl-]>C(O)(C)(C)C.C(OCC)(=O)C.C([O-])(=O)C.[Cu+2].C([O-])(=O)C.O>[CH2:15]([N:12]1[CH:3]=[C:2]([CH2:1][NH2:4])[N:14]=[N:13]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 12152Benzyl azideHCID 11073648tert-butyl N-(prop-2-yn-1-yl)carbamateHCID 23667548Sodium Ascorbate

Product 1

HCID 12160907HCID 12160907, compound

Reagents, catalysts & solvents 4

HCID 8895Cupric acetateCatalystHCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A reaction mixture comprising of tert-butyl prop-2-yn-1-ylcarbamate (219 mg, 1.411 mmol), (azidomethyl)benzene (188 mg, 1.411 mmol), copper (II) acetate (25.6 mg, 0.141 mmol) and sodium L-ascorbate (55.9 mg, 0.282 mmol) in tert-butanol (20 ml)/water (20 ml) was stirred for 18 hours at room temperature. The reaction mixture was acidified to pH1 using 6M HCl, then saturated with solid NaCl. The reaction mixture was concentrated under pressure to yield a green aqueous solution. The mixture was diluted with ethyl acetate and the organics were removed and dried (MgSO4). Concentration under reduced pressure afforded an orange oil. The oil was loaded on to a 10 g SCX2 cartridge, and this was washed with water and methanol. The product was then eluted with 2M ammonia in methanol. The solution was then concentrated to afford the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated under pressure
  2. customto yield a green aqueous solution
  3. customthe organics were removed
  4. dry with materialdried (MgSO4)
  5. concentrationConcentration under reduced pressure
  6. customafforded an orange oil
  7. washthis was washed with water and methanol
  8. washThe product was then eluted with 2M ammonia in methanol
  9. concentrationThe solution was then concentrated

Sources & evidence

ORD record
ord-662518d941664889978e6c4485998b91
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

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