Triethylamine → Methyl 2-{[2-(methoxyacetylamino)-5-methylbenzyl]-(4-methoxy-benzenesulfonyl)-amino}acrylate

HRID 1420611Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1420611
O[CH2:2][CH:3]([N:8]([S:18]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)(=[O:20])=[O:19])[CH2:9][C:10]1[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:11]=1[NH2:17])[C:4]([O:6][CH3:7])=[O:5].C(N(CC)CC)C.[CH3:36][O:37][CH2:38][C:39](Cl)=[O:40]>ClCCl>[CH3:36][O:37][CH2:38][C:39]([NH:17][C:11]1[CH:12]=[CH:13][C:14]([CH3:16])=[CH:15][C:10]=1[CH2:9][N:8]([S:18]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)(=[O:20])=[O:19])[C:3](=[CH2:2])[C:4]([O:6][CH3:7])=[O:5])=[O:40]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 96623Methoxyacetyl chlorideHCID 18612905Methyl 3-Hydroxy-2-[(4-methoxybenzenesulfonyl)-(2-amino-5-methylbenzyl)amino]propionate

Produkt 1

HCID 18613017Methyl 2-{[2-(methoxyacetylamino)-5-methylbenzyl]-(4-methoxy-benzenesulfonyl)-amino}acrylateAusbeute 107,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a cooled (0° C.) mixture of 1.598 g (3.91 mmol) of methyl 3-hydroxy-2-[(4-methoxybenzenesulfonyl)-(2-amino-5-methylbenzyl)amino]propionate and 1.97 g (19.5) mmol) of triethylamine in 15 ml of dichloromethane was added 0.787 ml (8.60 mmol) of methoxyacetylchloride. The mixture was stirred at room temperature overnight. The mixture was then diluted with CH2Cl2 and washed with H2O, 2N citric acid, H2O, brine and dried with Na2SO4. The solution was filtered through a thin pad of hydrous magnesium silicate and the filtrate concentrated to give 1.94 g of crude methyl 2-{[2-(methoxyacetylamino)-5-methylbenzyl]-(4-methoxy-benzenesulfonyl)-amino}acrylate as a brown oil. Mass spectrum (ES) 463.4 (M+H).

Aufarbeitung

  1. temperatureTo a cooled
  2. washwashed with H2O, 2N citric acid, H2O, brine
  3. dry with materialdried with Na2SO4
  4. filtrationThe solution was filtered through a thin pad of hydrous magnesium silicate
  5. concentrationthe filtrate concentrated

Quellen und Nachweise

ORD-Eintrag
ord-027c86db395647f886b7b7733c5d9852
Quelldatensatz
uspto-grants-2000_06
Patentnummer
US06071903

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