6-Bromohexanenitrile → HCID 67147960, compound

HRID 2219050Notes

Reaction equation

HRID 2219050 reaction equation
C(OC(=O)[N:7]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]#[N:14])(C)(C)C.BrCCCCCC#N>Cl.CCO>[CH2:16]([O:15][N:7]1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1=[NH:14])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 810936-BromohexanenitrileHCID 87286888HCID 87286888, compound

Product 1

HCID 67147960HCID 67147960, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

Tert-butyl-(benzyloxy)-(5-cyanopentyl)-carbamate (synthesized following the procedure described in EXAMPLE 1-Step 1a starting from 6-bromohexanenitrile) was dissolved in a saturated solution of HCl in EtOH and the mixture was stirred for 45 minutes. Nitrogen was bubbled into the solution to remove HCl in excess. The solvent was removed under reduced pressure and the residue, dissolved in 1,4-dioxane, was treated with triethylamine to adjust pH at 10. Ethanol was removed and the title compound containing an excess of triethylammonium chloride and ethyl 6-[(benzyloxy)amino]hexanoate was used without further purification. The analytical sample was purified by preparative RP-HPLC, using water (0.1% TFA) and acetonitrile (0.1% TFA) as eluents (column C18). The pooled product fractions were lyophilized.

Workup

  1. customNitrogen was bubbled into the solution
  2. customto remove HCl in excess
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe residue, dissolved in 1,4-dioxane
  5. additionwas treated with triethylamine
  6. customEthanol was removed
  7. additionthe title compound containing an excess of triethylammonium chloride and ethyl 6-[(benzyloxy)amino]hexanoate
  8. customwas used without further purification
  9. customThe analytical sample was purified by preparative RP-HPLC

Sources & evidence

ORD record
ord-91853f860afc49b9bf314a8601b9d26a
Source dataset
uspto-grants-2008_08
Patent number
US07414045B2

Reaction notes

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