Methanol → HCID 70059047, Verbindung

HRID 2230273

Reaktionsgleichung

Reaktionsgleichung von HRID 2230273
[CH3:1][C@@:2]([C:12]([OH:14])=[O:13])([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)[NH2:3].CO.[CH2:17]([Br:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>[OH-].[Na+].[O-]S([O-])(=O)=O.[Cu+2]>[BrH:24].[NH2:3][C:2]([CH3:1])([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:7][CH:6]=1)[C:12]([OH:14])=[O:13]

Komponenten

6

Edukt 3

HCID 887MethanolHCID 7498Benzyl BromideHCID 441350Metyrosine

Produkt 1

HCID 70059047HCID 70059047, VerbindungAusbeute 46,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24462Copper SulfateKatalysatorHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

A solution of α-methyltyrosine (Aldrich Chemical Co., 10.0 g, 51.2 mmol) in 50 mL of 2N NaOH solution was treated with 40 mL of a 0.5 M solution of aqueous CuSO4. The resulting solution was stirred for 45 minutes. The resulting solution was treated with 150 mL of methanol and benzyl bromide (6.7 mL, 56.3 mmol) and stirred for an additional 45 minutes at 50° C. The light purple precipitate which formed was collected by suction filtration and dried under vacuum. The isolated solid was suspended in water and treated with 13 mL of concentrated hydrochloric acid. The suspended solid was collected by filtration, washed sequentially with 1N HCl solution and ether and then dried under vacuum at 45° C. (96 hr) to give the product as an off-white solid (8.7 g, 46%), mp=228-231° C. (dec).

Aufarbeitung

  1. stirringstirred for an additional 45 minutes at 50° C
  2. customThe light purple precipitate which formed
  3. filtrationwas collected by suction filtration
  4. customdried under vacuum
  5. additiontreated with 13 mL of concentrated hydrochloric acid
  6. filtrationThe suspended solid was collected by filtration
  7. washwashed sequentially with 1N HCl solution and ether
  8. customdried under vacuum at 45° C. (96 hr)

Quellen und Nachweise

ORD-Eintrag
ord-51dd80ddf1a143069dc35a0ceaa7ab65
Quelldatensatz
uspto-grants-2002_07
Patentnummer
US06423689B1

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