Triethylamine → HCID 86727641, compound

HRID 519241Notes

Reaction equation

HRID 519241 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][C:10]([C:13](=O)[CH3:14])([CH3:12])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC(N1CC(C)(C(O)=O)C1)=O)(C)(C)C.C(N(CC)CC)C.O.[NH2:39][NH2:40]>CCO.O>[C:1]([O:5][C:6]([N:8]1[CH2:11][C:10]([C:13](=[N:39][NH2:40])[CH3:14])([CH3:12])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)HCID 532341941-(tert-Butoxycarbonyl)-3-methylazetidine-3-carboxylic acidHCID 86727642HCID 86727642, compound

Product 1

HCID 86727641HCID 86727641, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 3-acetyl-3-methyl-azetidine-1-carboxylic acid tert-butyl ester (prepared from 1-(tert-butoxycarbonyl)-3-methylazetidine-3-carboxylic acid using the similar procedure detailed in Preparation #4, Steps A-B, 0.10 g, 0.47 mmol) and triethylamine (0.5 mL, 3.8 mmol) in EtOH (2 mL) was added aqueous hydrazine hydrate (85%, 0.117 g, 2.34 mmol) and the solution was heated at reflux for 4 h. The reaction mixture was cooled to ambient temperature and poured into water. The mixture was extracted with DCM (3×15 mL) and the combined organic phase was washed with brine (10 mL) and concentrated in vacuo to give 3-(1-hydrazono-ethyl)-3-methyl-azetidine-1-carboxylic acid tert-butyl ester (0.076 g, 71%), which was used directly in the next step without further purification. TLC: Rf=0.15 (eluting with 50% EtOAc in petroleum ether).

Workup

  1. temperaturethe solution was heated
  2. temperatureat reflux for 4 h
  3. extractionThe mixture was extracted with DCM (3×15 mL)
  4. washthe combined organic phase was washed with brine (10 mL)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cc5002d232664cb4bb5f052e8f67f97c
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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