Methylhydrazine → 2-Azaalanylalanine ethyl ester

HRID 437127Notes

Reaction equation

HRID 437127 reaction equation
[CH3:1][NH:2][NH2:3].C([N:6]([CH2:9][CH3:10])[CH2:7]C)C.[CH2:11]([O:13][C:14](CCN=C=O)=[O:15])[CH3:12].[O:21]1CCCC1>>[CH2:11]([O:13][C:14](=[O:15])[C@H:9]([CH3:10])[NH:6][C:7](=[O:21])[N:2]([CH3:1])[NH2:3])[CH3:12]

Participants

5

Reactant 4

HCID 6061MethylhydrazineHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 2733373Ethyl 3-isocyanatopropanoate

Product 1

HCID 227981162-Azaalanylalanine ethyl ester

Procedure

To a stirred solution of methylhydrazine (0.07 mole) and triethylamine (0.06 mole) in dry tetrahydrofuran (100 ml) at 0° to 5° C. is added (1-ethoxycarbonyl)-ethylisocyanate (0.06 mole) over a period of 1 hour. The reaction mixture is allowed to warm to room temperature for 1 hour and filtered. The filtrate is evaporated to dryness and the residue is recrystallized from ether to give pure 2-azaalanylalanine ethyl ester, m.p. 77° -79.5° C.

Workup

  1. filtrationfiltered
  2. customThe filtrate is evaporated to dryness
  3. customthe residue is recrystallized from ether

Sources & evidence

ORD record
ord-5506246383a046aca87f0f07961422d6
Source dataset
uspto-grants-1977_06
Patent number
US04029772

Reaction notes

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