Oxalyl chloride → HCID 12924680, compound

HRID 1633442Notes

Reaction equation

HRID 1633442 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 a 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 a 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-4aa20f221ab2481d97c59698d554af1b
Source dataset
uspto-grants-2003_01
Patent number
US06503725B2

Reaction notes

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