Ethyl orthoformate → HCID 53418335, compound

HRID 1693529Notes

Reaction equation

HRID 1693529 reaction equation
[CH2:1]([O:3][C:4](=[O:9])[CH:5]([NH2:8])[C:6]#[N:7])[CH3:2].[CH:10](OCC)(OCC)OCC.[CH:20]1([NH2:23])[CH2:22][CH2:21]1>C(#N)C>[CH2:1]([O:3][C:4]([C:5]1[N:8]=[CH:10][N:23]([CH:20]2[CH2:22][CH2:21]2)[C:6]=1[NH2:7])=[O:9])[CH3:2]

Participants

5

Reactant 3

HCID 31214Ethyl orthoformateHCID 69828CyclopropylamineHCID 288716Ethyl 2-amino-2-cyanoacetate

Product 1

HCID 53418335HCID 53418335, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of amino-cyano-acetic acid ethyl ester (333 mg, 2.6 mmol) and triethyl orthoformate (454 μL, 2.73 mmol) in acetonitrile is heated at reflux for 45 min. After cooled down to room temperature, cyclopropylamine (180 μL, 2.6 mmol) is added. After stirred at room temperature overnight, the solution is concentrated and purified with chromatography. The desired product is obtained a white solid as product (290 mg, 57% yield). 1H NMR (CDCl3) δ 7.08 (s, 1H), 5.01 (b, 2H), 4.27 (q, 2H), 2.95 (m, 1H), 1.31 (t, 3H), 1.04 (m, 2H), 0.91 (m, 2H); m/z 196.1 (M+H4).

Workup

  1. temperatureat reflux for 45 min
  2. concentrationthe solution is concentrated
  3. custompurified with chromatography

Sources & evidence

ORD record
ord-9e05c368b54d4fe3ba7c2f00ad680f11
Source dataset
uspto-grants-2012_04
Patent number
US08158634B2

Reaction notes

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