Dimethylbarbituric acid → HCID 53415290, compound

HRID 1755039Notes

Reaction equation

HRID 1755039 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][C:10]([C:19]#[N:20])([N:12](CC=C)CC=C)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN1C(=O)CC(=O)N(C)C1=O.C(=O)(O)[O-].[Na+]>ClCCl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:9][C:10]([NH2:12])([C:19]#[N:20])[CH2:11]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 69860Dimethylbarbituric acidHCID 516892Sodium BicarbonateHCID 66817844HCID 66817844, compound

Product 1

HCID 53415290HCID 53415290, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 3-cyano-3-diallylamino-azetidine 1-carboxylic acid tert-butyl ester (143.5 mg, 0.5174 mmol), 1,3-dimethylbarbituric acid (242.5 mg, 1.553 mmol) and tetrakis(triphenylphosphine)palladium(0) (30.3 mg, 0.0262 mmol) in dichloromethane (1.3 ml) was stirred at 40° C. for five hours. A saturated aqueous sodium bicarbonate solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was then dried over MgSO4 and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give 3-amino-3-cyano-azetidine-1-carboxylic acid tert-butyl ester (98 mg, 96%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe organic layer was then dried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-56e5bb26896d46f1857352e5c56f9b90
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

Loading…