Glycine ethyl ester, hydrochloride → HCID 69460905, compound

HRID 1297107Notes

Reaction equation

HRID 1297107 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([O:10][CH3:11])=[CH:4][C:3]=1[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:13].Cl.N[CH2:22]C(OCC)=O>N1C=CC=CC=1>[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([O:10][CH2:11][CH3:22])=[CH:4][C:3]=1[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:13]

Participants

4

Reactant 2

HCID 2723640Glycine ethyl ester, hydrochloride2×HCID 7148512HCID 7148512, compound

Product 1

HCID 69460905HCID 69460905, compoundYield 46.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Heat under reflux for 36 hours under an inert atmosphere a mixture of 4.5 g (17.6 mmol) of (2-amino-4,5-dimethoxyphenyl)(phenyl)methanone (XXIaa), 5 g (36 mmol) of ethyl glycinate hydrochloride, and 30 ml of anhydrous pyridine. Add four 2.5 g (18 mmol) fractions of ethyl glycinate hydrochloride, every 6 hours. Allow to equilibrate to room temperature. Evaporate to dryness. Add 200 ml of water. Extract three times with 300 ml of dichloromethane. Dry the organic fractions on Na2SO4 Purify by chromatography (AcOEt 3/hexane 1/3% triethylamine). Recrystallize in EtOH/EtO2. One obtains 2.2 g of the abovenamed product in the form of colorless crystals. Yield: 43%. M:248–250° C. 1H-NMR (CDCl3, 200 MHz): d 3.71 (s, 3H, OCH3), 3.95 (s, 3H, OCH3), 4.31 (s, 2H, CH2), 6.64 (s, 1H Ar), 6.70 (s, 1H Ar), 7.27–7.59 (m, 5H Ar), 9.40 (s, 1H exchangeable, —NH).

Workup

  1. temperatureHeat
  2. temperatureunder reflux for 36 hours under an inert atmosphere
  3. customevery 6 hours
  4. customto equilibrate to room temperature
  5. customEvaporate to dryness
  6. additionAdd 200 ml of water
  7. extractionExtract three times with 300 ml of dichloromethane
  8. customDry the organic fractions on Na2SO4
  9. customPurify by chromatography (AcOEt 3/hexane 1/3% triethylamine)
  10. customRecrystallize in EtOH/EtO2

Sources & evidence

ORD record
ord-0cacfac258cb48d582109c45b95bc69c
Source dataset
uspto-grants-2007_07
Patent number
US07250410B2

Reaction notes

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