Trityl chloride → HCID 178498696, compound

HRID 1660764Notes

Reaction equation

HRID 1660764 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:9])[C@@H:5]([CH2:7]O)[NH2:6].C(N(CC)CC)C.[C:17](Cl)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(Cl)(Cl)Cl>[C:17]([N@@:6]1[CH2:7][CH:5]1[C:4]([O:3][CH3:2])=[O:9])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 11446470D-Serine methyl ester hydrochloride

Product 1

HCID 178498696HCID 178498696, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

200 g of D-serine methyl ester hydrochloride was added to 1.8 L of chloroform, and the reaction solution was cooled to 0° C., to which 448 mL of triethylamine was then slowly added. 358.4 g of trityl chloride was slowly added to the reaction mixture which was then stirred for 1 hour. The reaction mixture was warmed to room temperature, and 1 L of chloroform was added thereto, followed by washing with 2.5 L of water. The organic layer was dried over magnesium sulfate and cooled to 0° C., to which 484 mL of triethylamine and 15.7 g of 4-methylaminopyridine were then sequentially and slowly added. The reaction mixture was stirred for 5 min and 139 mL of methane sulfonyl chloride was slowly added thereto. The reaction mixture was warmed to room temperature, stirred for another 4 hours and then refluxed for 12 hours. The reaction mixture was cooled to room temperature, and washed with 4 L of water and then 3 L of brine. The organic layer was dried over magnesium sulfate and concentrated to dryness under reduced pressure. 3 L of ethanol was added to the resulting residue which was then stirred. The resulting solids were filtered to afford 329 g of the title compound.

Workup

  1. additionwas then slowly added
  2. washby washing with 2.5 L of water
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. temperaturecooled to 0° C., to which 484 mL of triethylamine and 15.7 g of 4-methylaminopyridine
  5. additionsequentially and slowly added
  6. stirringThe reaction mixture was stirred for 5 min
  7. addition139 mL of methane sulfonyl chloride was slowly added
  8. temperatureThe reaction mixture was warmed to room temperature
  9. stirringstirred for another 4 hours
  10. temperaturerefluxed for 12 hours
  11. temperatureThe reaction mixture was cooled to room temperature
  12. washwashed with 4 L of water
  13. dry with materialThe organic layer was dried over magnesium sulfate
  14. concentrationconcentrated to dryness under reduced pressure
  15. addition3 L of ethanol was added to the resulting residue which
  16. stirringwas then stirred
  17. filtrationThe resulting solids were filtered

Sources & evidence

ORD record
ord-de638b4db6e944868fad2a7117b2719f
Source dataset
uspto-grants-2011_10
Patent number
US08030315B2

Reaction notes

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