6-Bromohexanenitrile → HCID 67147960, compound

HRID 2426263Notes

Reaction equation

HRID 2426263 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-8d5bb3e117a44565891bb0b62d34489f
Source dataset
uspto-grants-2011_06
Patent number
US07968553B2

Reaction notes

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