Hydrochloric Acid → HCID 66988057, compound

HRID 540422Notes

Reaction equation

HRID 540422 reaction equation
C1(C(C2C=CC=CC=2)=[N:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])C=CC=CC=1.CC(C)([O-])C.[K+].[CH3:27][O:28][C:29]1[CH:37]=[CH:36][C:32]([C:33]([Cl:35])=[O:34])=[CH:31][CH:30]=1.Cl>O1CCCC1>[ClH:35].[NH2:8][CH:9]([C:33]([C:32]1[CH:36]=[CH:37][C:29]([O:28][CH3:27])=[CH:30][CH:31]=1)=[O:34])[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7477p-Anisoyl chlorideHCID 319508Ethyl 2-(diphenylmethyleneamino)acetateHCID 23665647Potassium tert-butoxide

Product 1

HCID 66988057HCID 66988057, compoundYield 108%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-70 °C

Procedure

5 g (18.6 mmol) of ethyl N-(diphenylmethylene)glycinate in solution in 20 ml of tetrahydrofuran are added to a solution of 18.7 ml (18.6 mmol) of 1N potassium tert-butoxide in 20 ml of tetrahydrofuran cooled to −70° C. After stirring for 30 minutes, this mixture is added to a solution containing 3.2 g (18.6 mmol) of 4-methoxybenzoyl chloride in 20 ml of tetrahydrofuran at −70° C. One hour after the addition, the reaction medium is hydrolysed with a 1N aqueous solution of hydrochloric acid and concentrated. The residue is taken up in water and extracted with diethyl ether. The organic phase is dried over magnesium sulphate and the solvent is then evaporated off. 5.5 g of ethyl 2-amino-3-(4-methoxyphenyl)-3-oxopropanoate hydrochloride are obtained with a quantitative yield.

Workup

  1. additionthis mixture is added to a solution
  2. additionOne hour after the addition
  3. concentrationconcentrated
  4. extractionextracted with diethyl ether
  5. dry with materialThe organic phase is dried over magnesium sulphate
  6. customthe solvent is then evaporated off

Sources & evidence

ORD record
ord-1111e9371ee84d4faa6bd9d7a02fad31
Source dataset
uspto-grants-2014_10
Patent number
US08871187B2

Reaction notes

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