Methylhydrazine → 2-Azaalanyllactyllactic acid ethyl ester

HRID 461790Notes

Reaction equation

HRID 461790 reaction equation
[C:1](Cl)(Cl)=[O:2].[C:5]([C:10]([CH3:17])([OH:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])(=[O:9])[CH:6]([CH3:8])[OH:7].C(N(CC)CC)C.[CH3:25][NH:26][NH2:27]>C1C=CC=CC=1.O1CCCC1>[CH2:14]([O:13][C:11](=[O:12])[C:10]([C:5](=[O:9])[CH:6]([CH3:8])[OH:7])([CH2:17][C:1](=[O:2])[N:26]([CH3:25])[NH2:27])[OH:16])[CH3:15]

Participants

7

Reactant 4

HCID 6061MethylhydrazineHCID 6371PhosgeneHCID 8471Triethylamine2×HCID 87238677Ethyl lactyllactate

Product 1

HCID 1317109832-Azaalanyllactyllactic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

To a mixture of 50 ml of 12.5% phosgene in benzene and 50 ml of tetrahydrofuran which has been cooled to 0° to +5° is added slowly a mixture of 0.05 mole of ethyl lactyllactate and 0.05 mole of triethylamine in 50 of tetrahydrofuran. The above reaction mixture is stirred at 0° to +5° for 2 hours and is then added dropwise to a mixture of 3 gm of methylhydrazine and 0.05 moles of triethylamine in 50 ml of tetrahydrofuran which has been cooled to 0° to +5°. After stirring for 3 hours the reaction mixture is filtered to remove triethylamine hydrochloride. The filtrate is then concentrated in vacuo to give 13.6 gm of crude product. Chromatography on 700 gm of silica gel and elution with methanol/methylene chloride give 6.9 gm of 2-azaalanyllactyllactic acid ethyl ester.

Workup

  1. temperaturehas been cooled to 0° to +5°
  2. additionis added slowly
  3. customThe above reaction mixture
  4. temperaturehas been cooled to 0° to +5°
  5. stirringAfter stirring for 3 hours the reaction mixture
  6. filtrationis filtered
  7. customto remove triethylamine hydrochloride
  8. concentrationThe filtrate is then concentrated in vacuo
  9. customto give 13.6 gm of crude product
  10. washChromatography on 700 gm of silica gel and elution with methanol/methylene chloride

Sources & evidence

ORD record
ord-b48679d1c1f3432f9ef13f50d2a1279d
Source dataset
uspto-grants-1977_12
Patent number
US04064236

Reaction notes

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