Tetrabutylammonium Hydroxide → (2S)-3-(3,4-Dihydroxyphenyl)-2-[(tert-butoxycarbonyl)amino]propanoic Acid, Tetrabutylammonium Salt

HRID 2088282

Reaktionsgleichung

Reaktionsgleichung von HRID 2088282
[C:1]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:21]=[C:19]([OH:20])[C:17]([OH:18])=[CH:16][CH:15]=1)[C:10]([OH:12])=[O:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[OH-].[CH2:23]([N+:27]([CH2:36][CH2:37][CH2:38][CH3:39])([CH2:32][CH2:33][CH2:34][CH3:35])[CH2:28][CH2:29][CH2:30][CH3:31])[CH2:24][CH2:25][CH3:26]>CO>[CH2:36]([N+:27]([CH2:23][CH2:24][CH2:25][CH3:26])([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:32][CH2:33][CH2:34][CH3:35])[CH2:37][CH2:38][CH3:39].[OH:20][C:19]1[CH:21]=[C:14]([CH2:13][C@H:9]([NH:8][C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[C:10]([O-:12])=[O:11])[CH:15]=[CH:16][C:17]=1[OH:18]

Komponenten

4

Edukt 2

HCID 2723671Tetrabutylammonium HydroxideHCID 14217229N-(tert-Buloxycarbonyl)-3,4-dihydroxy-L-phenylalanine

Produkt 1

HCID 46899461(2S)-3-(3,4-Dihydroxyphenyl)-2-[(tert-butoxycarbonyl)amino]propanoic Acid, Tetrabutylammonium SaltAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
4 °C

Versuchsvorschrift

A solution of N-Boc-(L)-Dopa (175 g, 0.59 mol) in methanol (1 L) was cautiously mixed with a methanolic solution of tetrabutylammonium hydroxide (1.0 M, 0.55 L) at 0° C. for 30 min. The mixture was then concentrated under reduced pressure and dried by azeotroping twice with toluene. The residue was crystallized after cooling at 4° C. for 16 h. The resulting crystalline solid was washed with acetone (400 mL×3), collected on a Buchner funnel, and then dried under high vacuum to afford 245 g (83% yield) of the title compound 1a. 1H NMR (400 MHz, DMSO-d6): δ 0.94 (t, J=7.6 Hz, 12H), 1.30 (m, 17H), 1.60 (m, 8H), 3.18 (m, 8H), 4.58 (m, 1H), 5.68 (d, J=5.6 Hz, 1H), 6.30 (d, J=7.6 Hz, 1H), 6.46 (d, J=8.0 Hz, 1H), 6.51 (s, 1H), 8.85 (s, 1H): 8.94 (s, 1H).

Aufarbeitung

  1. concentrationThe mixture was then concentrated under reduced pressure
  2. customdried
  3. customby azeotroping twice with toluene
  4. customThe residue was crystallized
  5. washThe resulting crystalline solid was washed with acetone (400 mL×3)
  6. customcollected on a Buchner funnel
  7. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-440299f454f14416bb5c56c767d4d92b
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08435562B2

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