Ethylmorpholine → HCID 22923964, compound

HRID 2258001Notes

Reaction equation

HRID 2258001 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]([C:18]([O:20][CH2:21][CH3:22])=[O:19])([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:9][C:10]([OH:12])=O)=[CH:3][CH:2]=1.Cl.[CH3:24][O:25][C:26](=[O:29])[CH2:27][NH2:28].[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.C(N1CCOCC1)C>CN(C)C=O>[CH3:24][O:25][C:26](=[O:29])[CH2:27][NH:28][C:10](=[O:12])[CH2:9][C:8]([C:18]([O:20][CH2:21][CH3:22])=[O:19])([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:7][C:4]1[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 7525EthylmorpholineHCID 122755Glycine methyl ester hydrochlorideHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 22923961HCID 22923961, compound

Product 1

HCID 22923964HCID 22923964, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

9.27 g of 4-(4-pyridyl)-3,3-bisethoxycarbonylbutyric acid are dissolved in 600 ml of dimethylformamide. 3.69 g of glycine methyl ester hydrochloride, 8.78 g of TOTU and 11.5 ml of N-ethylmorpholine are then added successively. The mixture is stirred for 24 h and the solvent is then stripped off in vacuo. The oily residue is chromatographed on silica gel using ethyl acetate. The fractions containing the product are combined and concentrated.

Workup

  1. customThe oily residue is chromatographed on silica gel
  2. additionThe fractions containing the product
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-43b13bcef8974925863f72a3c41239af
Source dataset
uspto-grants-1997_08
Patent number
US05658935

Reaction notes

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