Chlorotrimethylsilane → HCID 22870460, compound

HRID 976013Notes

Reaction equation

HRID 976013 reaction equation
Cl.Cl.[NH2:3][C@@H:4]([CH2:8]/[CH:9]=[CH:10]/[CH2:11][C@H:12]([NH2:16])[C:13]([OH:15])=[O:14])[C:5]([OH:7])=[O:6].Cl.C[Si](Cl)(C)C.Cl[C:24]([O:26][CH2:27][CH:28]1[C:40]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[C:34]2[C:29]1=[CH:30][CH:31]=[CH:32][CH:33]=2)=[O:25]>C[Si](C)(C)N[Si](C)(C)C.C(Cl)Cl>[CH:39]1[C:40]2[CH:28]([CH2:27][O:26][C:24]([NH:3][C@@H:4]([CH2:8]/[CH:9]=[CH:10]/[CH2:11][C@H:12]([NH:16][C:24]([O:26][CH2:27][CH:28]3[C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][C:34]=4[C:35]4[C:40]3=[CH:39][CH:38]=[CH:37][CH:36]=4)=[O:25])[C:13]([OH:15])=[O:14])[C:5]([OH:7])=[O:6])=[O:25])[C:29]3[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:35]=2[CH:36]=[CH:37][CH:38]=1

Participants

6

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 343679-Fluorenylmethyl chloroformateHCID 86750550HCID 86750550, compound

Product 1

HCID 22870460HCID 22870460, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 13838HexamethyldisilazaneSolvent

Conditions

Temperature
0 °C

Procedure

The acid hydrochloride (S,S)-2,7-Diamino-E-oct-4-ene-1,8-dioic acid dihydrochloride (1.59 g, 5.8 mmol) was suspended in hexamethyldisilazane (20 ml) and 1 ml of trimethylsilyl chloride was added. Then the suspension was refluxed overnight. The solvent was removed under reduced pressure and the residue was dissolved in anhydrous methylene chloride. This solution was cooled to 0° C. and a solution of 9-fluorenylmethyl chloroformate (3.10 g, 12 mmol) in methylene chloride was added. The solution was stirred for 1 hour before the cooling bath was removed. The next morning the solvent was evaporated and the residue was dissolved in THF. Then the mixture was quenched with 1N aqueous HCl and the solution was stirred for two hours. The organic solvent was removed and the water phase was extracted with chloroform. The organic layer was dried over magnesium sulfate and evaporated. The residue was dissolved in methylene chloride and precipitated with ether.

Workup

  1. temperatureThen the suspension was refluxed overnight
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in anhydrous methylene chloride
  4. customwas removed
  5. customThe next morning the solvent was evaporated
  6. dissolutionthe residue was dissolved in THF
  7. customThen the mixture was quenched with 1N aqueous HCl
  8. stirringthe solution was stirred for two hours
  9. customThe organic solvent was removed
  10. extractionthe water phase was extracted with chloroform
  11. dry with materialThe organic layer was dried over magnesium sulfate
  12. customevaporated
  13. dissolutionThe residue was dissolved in methylene chloride
  14. customprecipitated with ether

Sources & evidence

ORD record
ord-d74d5efc062b4132812fb717c347f173
Source dataset
uspto-grants-1997_03
Patent number
US05610141

Reaction notes

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