HCID 19708737, compound → HCID 19708705, compound

HRID 725779Notes

Reaction equation

HRID 725779 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([S:12]([N:15]1[CH2:20][CH:19]3[CH2:21][CH:16]1[CH2:17][N:18]3C(OC(C)(C)C)=O)(=[O:14])=[O:13])=[CH:7]2>CCOC(C)=O>[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([S:12]([N:15]1[CH2:20][CH:19]3[CH2:21][CH:16]1[CH2:17][NH:18]3)(=[O:13])=[O:14])=[CH:7]2

Participants

3

Reactant 1

HCID 19708737HCID 19708737, compound

Product 1

HCID 19708705HCID 19708705, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-(5-chloro-2-naphthylsulfonyl)-5-tertiary butoxy carbonyl-2,5-diazabicyclo[2.2.1] heptane (0.50 g, 2 mmol) was dissolved in about 5 ml. EtOAc. HCl gas was bubbled through the solution, resulting in an immediate change of color from orange to yellow. HCl was bubbled in for 15 minutes more and a precipitate started forming at this time. After 30 minutes, the ice bath was removed. The reaction was complete at 2 hours. The precipitate was filtered and triturated with Et2O to give 0.37 g of an off-white powder, mp: 225°-2270° C.

Workup

  1. customHCl gas was bubbled through the solution
  2. customresulting in an immediate change of color from orange to yellow
  3. customHCl was bubbled in for 15 minutes more
  4. customa precipitate started forming at this time
  5. customthe ice bath was removed
  6. waitThe reaction was complete at 2 hours
  7. filtrationThe precipitate was filtered
  8. customtriturated with Et2O

Sources & evidence

ORD record
ord-f51364dbaab94a058f1c31085d065b89
Source dataset
uspto-grants-1998_01
Patent number
US05707985

Reaction notes

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