1,1,3,3-Tetramethylguanidine → HCID 13774519, compound

HRID 1622903Notes

Reaction equation

HRID 1622903 reaction equation
[NH2:1][C@H:2]([CH3:6])[C:3]([OH:5])=[O:4].CN(C)C(N(C)C)=N.C([O:18][CH2:19][C:20]([F:23])([F:22])[F:21])(=O)C>CO>[F:21][C:20]([F:23])([F:22])[C:19]([NH:1][C@H:2]([CH3:6])[C:3]([OH:5])=[O:4])=[O:18]

Participants

5

Reactant 3

HCID 664601,1,3,3-TetramethylguanidineHCID 71080D-AlanineHCID 1362562,2,2-Trifluoroethyl Acetate

Product 1

HCID 13774519HCID 13774519, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(R)-2-amino propionic acid (8.9 g, 0.1 mol) was dissolved in 100 ml of methanol, and 1,1,3,3-tetramethyl guanidine (15.6 g, 0.136 mol) was added. At room temperature, trifluoroethyl acetate (18.5 g, 0.13 mol) was added dropwise. After the completion of the addition, stirring is conducted to allow a reaction to proceed for 5 hours. Most solvent was removed by evaporation, and the residue was poured into 100 ml of water, acidified with 12 ml of concentrated hydrochloric acid, and extracted with ethyl acetate (3×60 ml). The organic phases were combined, washed with saturated brine, dried with anhydrous sodium sulfate, concentrated and crystallized, washed with 160 ml of hexane, filtered, and dried, obtaining 18.0 g of product. The yield was 97.3%. MS: m/z 185.1

Workup

  1. additionAfter the completion of the addition
  2. customa reaction
  3. customMost solvent was removed by evaporation
  4. additionthe residue was poured into 100 ml of water
  5. extractionextracted with ethyl acetate (3×60 ml)
  6. washwashed with saturated brine
  7. dry with materialdried with anhydrous sodium sulfate
  8. concentrationconcentrated
  9. customcrystallized
  10. washwashed with 160 ml of hexane
  11. filtrationfiltered
  12. customdried

Sources & evidence

ORD record
ord-735f9d8363294467bc358d982ecc50fb
Source dataset
uspto-grants-2014_07
Patent number
US08778948B2

Reaction notes

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