Triethylamine → HCID 178449215, compound

HRID 248614Notes

Reaction equation

HRID 248614 reaction equation
[C:1]([N:3]=[C:4](OC)[CH2:5][CH2:6][CH3:7])#[N:2].Cl.[CH3:11][O:12][C:13](=[O:16])[CH2:14][NH2:15].C(N(CC)CC)C>CO>[C:1]([N:3]=[C:4]([NH:15][CH2:14][C:13]([O:12][CH3:11])=[O:16])[CH2:5][CH2:6][CH3:7])#[N:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 122755Glycine methyl ester hydrochlorideHCID 15477524Methyl N-cyanobutanimidate

Product 1

HCID 178449215HCID 178449215, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
5 °C

Procedure

Methyl N-cyanobutyrimidate (240 g, 1.90 mol) from Example 2 was dissolved in absolute methanol (1.5 L) and glycine methyl ester HCl (250 g, 1.99 mol) added to the reaction mixture. The suspension was cooled to 5° C. and triethylamine (211 g, 2.09 mol) added over a period of 15 minutes. The resulting solution was stirred at 20° C. for 17 hours, then concentrated under reduced pressure to an oily-solid residue (690 g). The residue was taken up in ethyl acetate and the insoluble salts removed by filtration. The filtrate was washed with water followed by 10% aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and evaporated to dryness under reduced pressure. This product (370 g) was used in the next step without further purification.

Workup

  1. concentrationconcentrated under reduced pressure to an oily-solid residue (690 g)
  2. customthe insoluble salts removed by filtration
  3. washThe filtrate was washed with water
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customevaporated to dryness under reduced pressure
  6. customThis product (370 g) was used in the next step without further purification

Sources & evidence

ORD record
ord-7a9959756ba844fdb8132f35f82bf94c
Source dataset
uspto-grants-1993_05
Patent number
US05210211

Reaction notes

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