Ethyl chloroformate → HCID 20379307, compound

HRID 2051615Notes

Reaction equation

HRID 2051615 reaction equation
ClC(OCC)=O.[C:7]([O:11][C:12]([NH:14][CH2:15][C:16]([OH:18])=O)=[O:13])([CH3:10])([CH3:9])[CH3:8].I.[NH:20]=[C:21]1[N:25]([CH3:26])[CH2:24][CH2:23][S:22]1>C(Cl)Cl.C(N(CC)CC)C>[CH3:26][N:25]1[CH2:24][CH2:23][S:22][C:21]1=[N:20][C:16](=[O:18])[CH2:15][NH:14][C:12]([O:11][C:7]([CH3:8])([CH3:9])[CH3:10])=[O:13]

Participants

6

Reactant 3

HCID 10928Ethyl chloroformateHCID 78288N-(tert-butoxycarbonyl)glycineHCID 27705073-Methyl-1,3-thiazolidin-2-imine hydroiodide

Product 1

HCID 20379307HCID 20379307, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent2×

Conditions

Temperature
-5 °C

Procedure

Ethyl chloroformate (0.25 ml.) at -5° C. was added to a solution of 350 mg. of t-butoxycarbonylaminoacetic acid and 0.4 ml. of triethylamine in 10 ml. of methylene chloride at -5° C. After stirring 5 minutes at -5° C. there was added a solution of 610 mg. of 2-imino-3-methylthiazolidine hydrogen iodide and 1.0 ml. of triethylamine in 10 ml. of methylene chloride also at -5° C. Stirring was continued at -5° C. for 15 minutes and one hour at room temperature. The reaction mixture was washed with 40 ml. of 20% (w/v) citric acid solution, sodium bicarbonate solution, and water, dried and concentrated to dryness. The residue was triturated with ether, petroleum ether and ether and finally collected to give pure N-(3-methylthiazolidin-2-ylidene)-t-butoxycarbonylaminoacetamide.

Workup

  1. customat -5° C
  2. additionthere was added a solution of 610 mg
  3. customalso at -5° C
  4. stirringStirring
  5. waitwas continued at -5° C. for 15 minutes and one hour at room temperature
  6. washThe reaction mixture was washed with 40 ml
  7. dry with materialof 20% (w/v) citric acid solution, sodium bicarbonate solution, and water, dried
  8. concentrationconcentrated to dryness
  9. customThe residue was triturated with ether, petroleum ether and ether
  10. customfinally collected

Sources & evidence

ORD record
ord-282b45b8f3454126bcf896e4c191b799
Source dataset
uspto-grants-1980_01
Patent number
US04181661

Reaction notes

Loading…