Acetic Anhydride → HCID 67034203, compound

HRID 1944250Notes

Reaction equation

HRID 1944250 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]([NH:14][NH2:15])=[O:13])[CH2:8][CH2:7]1)=[O:5])[CH3:2].[C:16](OC(=O)C)(=O)[CH3:17].P(Cl)(Cl)(Cl)=O.C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.CCOC(C)=O>[CH2:1]([O:3][C:4]([CH:6]1[CH2:7][CH2:8][N:9]([C:12]2[O:13][C:16]([CH3:17])=[N:15][N:14]=2)[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 67033215HCID 67033215, compound

Product 1

HCID 67034203HCID 67034203, compoundYield 20.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-hydrazinocarbonyl-piperidine-4-carboxylic acid ethyl ester (215 mg, 0.999 mmol) in THF (2 ml) was added acetic anhydride (188 μl, 2.00 mmol). After stirring for 5 minutes at rt phosphorus oxychloride (182 μl, 2.00 mmol) was added and the reaction mixture was stirred for 5 days at RT. The reaction mixture was added dropwise onto a 1 M solution of sodium carbonate (10 ml). The mixture was diluted with EtOAc (15 ml). The aq. layer was extracted with EtOAc (15 ml). The organic layers were washed with brine (15 ml) and dried over Na2SO4. A column chromatography (SiO2, EtOAc/Hept 1/1 to Hept/MeOH 9/1) yielded 48 mg (20%) of the title product as a light brown oil. MS m/e: 240.3 [M+H]+

Workup

  1. additionwas added
  2. extractionThe aq. layer was extracted with EtOAc (15 ml)
  3. washThe organic layers were washed with brine (15 ml)
  4. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-21cf38da60fc4ed2b687e84ac1404f5e
Source dataset
uspto-grants-2013_03
Patent number
US08394834B2

Reaction notes

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