Ethyl 2-ethoxyethylidene-cyanoacetate → HCID 21076915, compound

HRID 1455147Notes

Reaction equation

HRID 1455147 reaction equation
[C:1]([O:5][C:6](=[O:22])[NH:7][C@@H:8]([C:12](=[NH:21])[NH:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH:9]([CH3:11])[CH3:10])([CH3:4])([CH3:3])[CH3:2].C(O[CH2:26][CH:27]=[C:28]([C:34]#[N:35])[C:29](OCC)=[O:30])C>CCO>[C:1]([O:5][C:6](=[O:22])[NH:7][CH:8]([C:12]1[N:13]([CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:29](=[O:30])[C:28]([C:34]#[N:35])=[C:27]([CH3:26])[N:21]=1)[CH:9]([CH3:11])[CH3:10])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 57299996Ethyl 2-ethoxyethylidene-cyanoacetateHCID 178448380HCID 178448380, compound

Product 1

HCID 21076915HCID 21076915, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of [(R)-1-(N-Benzyl-carbamimidoyl)-2-methyl-propyl]-carbamic acid t-butyl ester (14.16 g, 46 mMol) in EtOH (50 mL) was added Ethyl 2-ethoxyethylidene-cyanoacetate (8.4 g, 46 mMol). The reaction was refluxed for 18 h, cooled to RT and concentrated under vacuum. Purification by flash chromatography on silica gel (5% EtOAc, CH2Cl2) followed by crystallization from EtOAc, hexane and Et2O, pet. ether gave the title compound (8.03 g, 44%) as a white solid: MS (ES) m/e 397.2 (M+H)+.

Workup

  1. temperatureThe reaction was refluxed for 18 h
  2. concentrationconcentrated under vacuum
  3. customPurification by flash chromatography on silica gel (5% EtOAc, CH2Cl2)
  4. customfollowed by crystallization from EtOAc, hexane and Et2O, pet. ether

Sources & evidence

ORD record
ord-a8d4ed5cbc0c42d490b30a80d86c4171
Source dataset
uspto-grants-2009_01
Patent number
US07482343B2

Reaction notes

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