Reaction #5491

ord-0675e965fa4340e2acbd5041468c8136

Reaction equation

O=C1N[C@@H](C(=O)O)CCCCCC[C@@H]1CS
Trans 3-mercaptomethyl-2-oxo-1-azacyclodecane-10-carboxylic acid
CC(=O)Cl
Acetyl chloride
→
CC(=O)SC[C@H]1CCCCCC[C@H](C(=O)O)NC1=O
trans 3-(acetylthiomethyl)-2-oxo-1-azacyclodecane-10-carboxylic acid

Reactants

O=C1N[C@@H](C(=O)O)CCCCCC[C@@H]1CS
Trans 3-mercaptomethyl-2-oxo-1-azacyclodecane-10-carboxylic acid
CC(=O)Cl
Acetyl chloride

Reagents

None

Solvents

c1ccncc1
pyridine

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherThe reaction is quenched
  2. 2
    Temperatureby cooling to 0° C.
  3. 3
    workup.ADDITIONadding concentrated hydrochloric acid (20 mL)
  4. 4
    workup.ADDITIONdiluting with water
  5. 5
    Extractionextracting several times with ethyl acetate
  6. 6
    DryingThe combined organic layers are dried (MgSO4)
  7. 7
    Otherthe solvent is evaporated

Procedure

Trans 3-mercaptomethyl-2-oxo-1-azacyclodecane-10-carboxylic acid (0.75 g, 3.06 mmol) is dissolved in pyridine (20 mL). Acetyl chloride (0.26 g, 3.37 mmol) is added, and the reaction is stirred at room temperature overnight. The reaction is quenched by cooling to 0° C., adding concentrated hydrochloric acid (20 mL), diluting with water, and extracting several times with ethyl acetate. The combined organic layers are dried (MgSO4), and the solvent is evaporated to give trans 3-(acetylthiomethyl)-2-oxo-1-azacyclodecane-10-carboxylic acid, MS:M+1=288.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05244889uspto-grants-1993_09