Oxalyl chloride → HCID 12924680, compound

HRID 1860232Notes

Reaction equation

HRID 1860232 reaction equation
[C:1]1([CH3:16])[CH:6]=[CH:5][C:4]([S:7]([NH:10][C@H:11]([C:13](O)=[O:14])[CH3:12])(=[O:9])=[O:8])=[CH:3][CH:2]=1.C(Cl)(=O)C([Cl:20])=O>CN(C)C=O.ClCCl>[S:7]([NH:10][C@H:11]([C:13]([Cl:20])=[O:14])[CH3:12])([C:4]1[CH:5]=[CH:6][C:1]([CH3:16])=[CH:2][CH:3]=1)(=[O:9])=[O:8]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 737622N-Tosyl-L-alanine

Product 1

HCID 12924680HCID 12924680, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

30.0 g of N-(p-toluenesulfonyl)-alanine and 6 to 7 drops of DMF (dimethylformamide) were dissolved in 100 ml of dichloromethane and 5 ml of oxalyl chloride was added dropwise. After stirring for 3 hours at room temperature the reaction mixture was evaporated down to an oily residue which was dissolved in 100 ml of dichloromethane. The dichloromethane was again evaporated and the resulting residue dissolved in 50 ml of dichloromethane followed by the addition of 100 ml hexane. After standing in the refrigerator overnight the crystals, so formed, were filtered and dried.

Workup

  1. customwas evaporated down to an oily residue which
  2. dissolutionwas dissolved in 100 ml of dichloromethane
  3. customThe dichloromethane was again evaporated
  4. dissolutionthe resulting residue dissolved in 50 ml of dichloromethane
  5. additionfollowed by the addition of 100 ml hexane
  6. customAfter standing in the refrigerator overnight
  7. customso formed
  8. filtrationwere filtered
  9. customdried

Sources & evidence

ORD record
ord-83ce42e340f1458b87723a83984fc184
Source dataset
uspto-grants-2003_03
Patent number
US06528652B1

Reaction notes

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