Toluene → HCID 131736346, compound

HRID 1055192Notes

Reaction equation

HRID 1055192 reaction equation
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.Cl.C([O:10][C:11](=[O:14])[CH2:12][NH2:13])C.[C:15]([O-:18])(O)=[O:16].[Na+].[C:20]1(C)C=CC=C[CH:21]=1>C(OCC)C>[C:15]([O:18][CH2:11][CH2:12][NH:13][C:4](=[O:5])[CH2:3][C:2](=[O:6])[CH3:1])(=[O:16])[CH3:20].[CH2:20]([N:13]([C:4](=[O:5])[CH2:3][C:2](=[O:6])[CH3:1])[CH2:12][C:11]([OH:10])=[O:14])[CH3:21]

Participants

6

Reactant 4

HCID 1140TolueneHCID 12661DiketeneHCID 516892Sodium BicarbonateHCID 2723640Glycine ethyl ester, hydrochloride

Product 1

HCID 131736346HCID 131736346, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 20.00 g (0.24 mol) diketene in 250 ml toluene was added dropwise at 0° C. to a solution of 33.21 g (0.24 mol) glycine ethyl ester hydrochloride (amino acetic ester hydrochloride). 40.00 g (0.48 mol) NaHCO3 were then added and the reaction mixture was stirred further at room temperature overnight. Since no starting material could be detected anymore by thin-layer chromatography, the reaction mixture was spun off, and the obtained solid was taken up in 100 ml diethylether, stirred for a short period of time, filtrated off and dried overnight under vacuum. 40.00 g of product was obtained as a white solid.

Workup

  1. stirringstirred for a short period of time
  2. filtrationfiltrated off
  3. customdried overnight under vacuum

Sources & evidence

ORD record
ord-a9356b51230e4cce84a80200597d2d1d
Source dataset
uspto-grants-2016_07
Patent number
US09394324B2

Reaction notes

Loading…