Triethylamine → HCID 178446442, compound

HRID 973667Notes

Reaction equation

HRID 973667 reaction equation
[C:1]([NH:3][C:4](=O)[CH:5](CC)[CH2:6][CH2:7][CH3:8])#[N:2].Cl.[NH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].C(N(CC)CC)C>C(O)C>[C:1]([N:3]=[C:4]([NH:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:5][CH2:6][CH2:7][CH3:8])#[N:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2723640Glycine ethyl ester, hydrochlorideHCID 86745198HCID 86745198, compound

Product 1

HCID 178446442HCID 178446442, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 100 mg (0.65 mmol) N-cyano-(ethylvaleramidate) (Example 1, Step B , in 2 mL absolute ethanol at room temperature was added 100 mg (0.72 mmol, 1.1 leq) ethyl glycinate hydrochloride followed by 0.30 mL triethylamine (220 mg, 2.16 mmol, 3.3 eq). The mixture was stirred at room temperature overnight then concentrated in vacuo to a gummy residue. The residue was treated with 20 mL of hexane/ethyl acetate (1:1), stirred vigorously, filtered, and the filtrate purified by medium pressure liquid chromatography on silica gel, eluting with hexane/ethyl acetate (1:1). The title compound (119 mg, 0.56 mmol, 87%) was thus obtained as a pale yellow oil that slowly solidified upon standing.

Workup

  1. concentrationthen concentrated in vacuo to a gummy residue
  2. additionThe residue was treated with 20 mL of hexane/ethyl acetate (1:1)
  3. stirringstirred vigorously
  4. filtrationfiltered
  5. customthe filtrate purified by medium pressure liquid chromatography on silica gel
  6. washeluting with hexane/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-fcde274ce8a94d1fa034f0e60bd74fb2
Source dataset
uspto-grants-1991_11
Patent number
US05064825

Reaction notes

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