Pyridine → ethyl 2-(N-(benzyloxy)-3-ethoxy-3-oxopropanamido)benzoate

HRID 1054213Notes

Reaction equation

HRID 1054213 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([OH:5])=O.[CH2:10]([O:17][NH:18][C:19]1[CH:29]=[CH:28][CH:27]=[CH:26][C:20]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.N1C=CC=CC=1.O=P(Cl)(Cl)Cl>C(#N)C.C(Cl)Cl>[CH2:10]([O:17][N:18]([C:19]1[CH:29]=[CH:28][CH:27]=[CH:26][C:20]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:3](=[O:5])[CH2:2][C:1]([O:7][CH2:8][CH3:9])=[O:6])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 24813Phosphorus oxychlorideHCID 70615Monoethyl malonateHCID 90257947Ethyl 2-(benzyloxyamino)benzoate

Product 1

HCID 90258228ethyl 2-(N-(benzyloxy)-3-ethoxy-3-oxopropanamido)benzoateYield 79%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

To a stirring solution of ethyl hydrogen malonate (0.6 g, 4.54 mmol) and ethyl 2-(benzyloxyamino)benzoate (1.12 g, 4.13 mmol) in acetonitrile (10 mL) was added pyridine (1.3 g, 16.51 mmol) and reaction mixture was cooled to 0-10° C. To this was added POCl3 (0.423 mL, 4.54 mmol), at 0-10° C. in 15-30 min. and stirring continued for 1 h. Reaction mixture was diluted with DCM and washed with water. Organic layer was separated and distilled out to get crude product which was column purified using 15% EtOAC in hexane to get titled compound in 79% yield.

Workup

  1. waitcontinued for 1 h
  2. customReaction mixture
  3. washwashed with water
  4. customOrganic layer was separated
  5. distillationdistilled out
  6. customto get crude product which
  7. custompurified

Sources & evidence

ORD record
ord-04f48a4203154c4887e5c39869aee50f
Source dataset
uspto-grants-2016_07
Patent number
US09394300B2

Reaction notes

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