Sodium Hydroxide → N-[[-(methoxycarbonyl)phenyl]sulfonyl]-3-(p-nitrophenyl)-D-alanine

HRID 234851

Reaktionsgleichung

Reaktionsgleichung von HRID 234851
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]([CH2:8][C@H:9]([C:11]([OH:13])=[O:12])[NH2:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH-].[Na+].C(=O)(O)[O-].[Na+].Cl[S:24]([C:27]1[CH:36]=[CH:35][CH:34]=[CH:33][C:28]=1[C:29]([O:31][CH3:32])=[O:30])(=[O:26])=[O:25]>O1CCOCC1>[CH3:32][O:31][C:29]([C:28]1[CH:33]=[CH:34][CH:35]=[CH:36][C:27]=1[S:24]([NH:10][C@@H:9]([C:11]([OH:13])=[O:12])[CH2:8][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:15][CH:14]=1)(=[O:26])=[O:25])=[O:30]

Komponenten

6

Edukt 4

HCID 14798Sodium HydroxideHCID 117830Benzoic acid, 2-(chlorosulfonyl)-, methyl esterHCID 516892Sodium BicarbonateHCID 679497p-Nitro-D-phenylalanine

Produkt 1

HCID 18659415N-[[-(methoxycarbonyl)phenyl]sulfonyl]-3-(p-nitrophenyl)-D-alanineAusbeute 71,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

2.3 g of p-nitro-D-phenylalanine are suspended in 25 ml of dioxan and treated with 10 ml of 1N sodium hydroxide solution and 1.7 g of sodium bicarbonate. A solution of 2.6 g of methyl 2-chlorosulfonylbenzoate in 22 ml of dioxanl is added dropwise thereto and the mixture is stirred at room temperature for 9 hours. The reaction mixture is poured into ice-cold 2N hydrochloric acid and extracted with ethyl acetate. The organic phase is washed with water, dried and evaporated. There are obtained 3.2 g of N-[[o-(methoxycarbonyl)phenyl]sulfonyl]-3-(p-nitrophenyl)-D-alanine.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic phase is washed with water
  3. customdried
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-a6f542f43f1e498d8b0f1bb87121e02b
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05595999

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