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(3,4-Dimethoxyphenyl)acetic acid → 2-(3,4-Dimethoxyphenyl)-3-{{[(3,4-dimethoxyphenyl)methyl]carbonyl}amino}propanoic acid ethyl ester

HRID 463708
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 463708
Cl.[CH2:2]([O:4][C:5](=[O:19])[CH:6]([CH2:17][NH2:18])[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([O:15][CH3:16])[CH:8]=1)[CH3:3].[OH-].[Na+].[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH2:32][C:33](Cl)=[O:34])[CH:27]=[CH:28][C:29]=1[O:30][CH3:31].S(Cl)(Cl)=O.COC1C=C(CC(O)=O)C=CC=1OC>C1(C)C=CC=CC=1.C(Cl)Cl.O>[CH2:2]([O:4][C:5](=[O:19])[CH:6]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([O:15][CH3:16])[CH:8]=1)[CH2:17][NH:18][C:33]([CH2:32][C:26]1[CH:27]=[CH:28][C:29]([O:30][CH3:31])=[C:24]([O:23][CH3:22])[CH:25]=1)=[O:34])[CH3:3]
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Komponenten

9

Edukt 5

HCID 7139(3,4-Dimethoxyphenyl)acetic acidHCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 3604458(3,4-Dimethoxyphenyl)acetyl chlorideHCID 69551005Ethyl 3-amino-2-(3,4-dimethoxyphenyl)propanoate hydrochloride

Produkt 1

HCID 13560525
2-(3,4-Dimethoxyphenyl)-3-{{[(3,4-dimethoxyphenyl)methyl]carbonyl}amino}propanoic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A mixture of 289 g of alpha-(aminomethyl)-3,4-dimethoxybenzeneacetic acid ethyl ester hydrochloride, 1000 ml of methylene chloride and 1000 ml of water was cooled to 0° and adjusted to pH 9.0 with 4N sodium hydroxide. A solution of 1000 ml of methylene chloride and 3,4-dimethoxyphenyl acetic acid chloride [previously prepared by the action of 400 ml of thionyl chloride on 215 g of 3,4-dimethoxyphenyl acetic acid in 500 ml of toluene at 50° for 1 hour and evaporation to dryness] was added concurrently with 4N sodium hydroxide maintaining a pH of 7.0-8.0. Upon completion of the acid chloride addition, the pH was maintained at 9.0 for 1 hour followed by acidification to pH 1.0 with 6N hydrochloric acid. The layers were separated and the aqueous layer extracted once with methylene chloride. The combined organic layers were washed once with excess saturated sodium bicarbonate solution, dried over sodium sulfate and evaporated in vacuo to give 430 g of 2-(3,4-dimethoxyphenyl)-3-{{[(3,4-dimethoxyphenyl)methyl]carbonyl}amino}propanoic acid ethyl ester as an oil.

Aufarbeitung

  1. temperaturewas cooled to 0°
  2. customevaporation to dryness]
  3. additionwas added concurrently with 4N sodium hydroxide maintaining a pH of 7.0-8.0
  4. additionUpon completion of the acid chloride addition
  5. temperaturethe pH was maintained at 9.0 for 1 hour
  6. customThe layers were separated
  7. extractionthe aqueous layer extracted once with methylene chloride
  8. washThe combined organic layers were washed once with excess saturated sodium bicarbonate solution
  9. dry with materialdried over sodium sulfate
  10. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-35d47ebdff3e4476a21a56f8a62db778
Quelldatensatz
uspto-grants-1985_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04544657

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