Sodium Acetate → 148550-19-0

HRID 1197588Notes

Reaction equation

HRID 1197588 reaction equation
Cl.[NH:2]=[C:3]([CH2:8][CH2:9]C)C(OC)=O.[C:11](O)(=O)[C:12](O)=O.[NH2:17][CH:18]([C:24]#[N:25])[C:19]([O:21][CH2:22][CH3:23])=[O:20].C([O-])(=O)C.[Na+]>C(O)C>[NH2:25][C:24]1[N:2]=[C:3]([CH2:8][CH2:9][CH2:11][CH3:12])[NH:17][C:18]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 6917117HCID 6917117, compoundHCID 86746837HCID 86746837, compound

Product 1

HCID 19106923148550-19-0Yield 69.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of methyl iminovalerate hydrochloride (4.8 g), ethyl 2-amino-2-cyanoacetate oxalate (4.0 g), anhydrous sodium acetate (9.1 g) and absolute ethanol (75 mL) was stirred at room temperature for 18 hours. Solids were removed by filtration and the filtrate was evaporated. The residue was partitioned between ethyl acetate and water. The ethyl acetate layer was washed with saturated NaCl, dried over MgSO4, and evaporated. Flash chromatography on silica gel, eluting with a gradient of dichloromethane-ethyl acetate (75:25) to ethyl acetate gives the title compound (2.7 g) as a pale yellow solid, mp 103°-106° C. MS (DEI) 211 (m).

Workup

  1. customSolids were removed by filtration
  2. customthe filtrate was evaporated
  3. customThe residue was partitioned between ethyl acetate and water
  4. washThe ethyl acetate layer was washed with saturated NaCl
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. washFlash chromatography on silica gel, eluting with a gradient of dichloromethane-ethyl acetate (75:25) to ethyl acetate

Sources & evidence

ORD record
ord-1271a4225e4b468ea826d7b8b2cdb1a4
Source dataset
uspto-grants-1994_01
Patent number
US05276048

Reaction notes

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