Tributylphosphine → HCID 18536080, compound

HRID 412129Notes

Reaction equation

HRID 412129 reaction equation
CC(OC(/N=N/C(OC(C)(C)C)=O)=O)(C)C.C(P(CCCC)CCCC)CCC.[CH2:30]([O:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1[C:44]1[CH:49]=[CH:48][C:47]([Cl:50])=[CH:46][C:45]=1[NH:51][C:52](=O)[CH2:53][NH:54][CH2:55][CH2:56][OH:57])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>CCOC(C)=O>[ClH:50].[CH2:30]([O:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1[C:44]1[CH:49]=[CH:48][C:47]([Cl:50])=[CH:46][C:45]=1[N:51]1[CH2:52][CH2:53][NH:54][CH2:55][C:56]1=[O:57])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 13831TributylphosphineHCID 6034084Di-tert-butyl diazene-1,2-dicarboxylateHCID 18536137HCID 18536137, compound

Product 1

HCID 18536080HCID 18536080, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent3×

Procedure

To a solution of di-tert-butylazodicarboxylate (5.557 g, 24.1 mmol) in 20 mL of EtOAc at 0° C. was added tributylphosphine (6.013 mL, 24.1 mmol) dropwise. After 10 minutes, a solution of the product from Step D (6.8548 g, 16.09 mmol) in 10 mL of EtOAc was added dropwise over 15 minutes, and the reaction was allowed to warm to room temperature. After one hour, the solution was poured into EtOAc, washed with sat. aq. NaHCO3 and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The crude product mixture was taken up in 30 mL of ether, 1N HCl/Ether was added (17 mL), and the solution was concentrated in vacuo. This was stirred in 50 mL of cold isopropanol over an ice bath for 30 minutes, and the resulting slurry was filtered and rinsed with cold isopropanol. The filtered solid was dried in vacuo next to P2O5 to provide the titled product as a white solid.

Workup

  1. waitAfter one hour
  2. washwashed with sat. aq. NaHCO3 and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. addition1N HCl/Ether was added (17 mL)
  7. concentrationthe solution was concentrated in vacuo
  8. filtrationthe resulting slurry was filtered
  9. washrinsed with cold isopropanol
  10. dry with materialThe filtered solid was dried in vacuo next to P2O5

Sources & evidence

ORD record
ord-838f96cc1bc74133bda93d62a0479eec
Source dataset
uspto-grants-2003_05
Patent number
US06562823B1

Reaction notes

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