Hydrogen Bromide → 2-Naphthylalanine

HRID 1482461Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1482461
Br.C[N+:3]1(CC2CC2)[C@@H:13]2[CH2:14][C:15]3[CH:20]=[CH:19]C(O)=C4O[C@H:7]5[C:8]([CH2:10]C[C@:12]2([OH:23])[C@:6]5([C:16]=34)[CH2:5][CH2:4]1)=O.[Br-].C1C2C[C@H]3N(CC4CC4)CC[C@]45[C@H](C(CC[C@@]34O)=O)[O:47]C(C=25)=C(O)C=1>>[NH2:3][C@H:13]([C:12]([OH:23])=[O:47])[CH2:14][C:15]1[CH:16]=[C:6]2[C:7]([CH:8]=[CH:10][CH:4]=[CH:5]2)=[CH:19][CH:20]=1

Komponenten

4

Edukt 3

HCID 260Hydrogen Bromide2×HCID 5360515NaltrexoneHCID 5361917Methylnaltrexone Bromide

Produkt 1

HCID 1859152-Naphthylalanine

Versuchsvorschrift

The entry for Example 4 in Table 3 represents the effect of the addition of acid (0.1 equiv. HBr). Incorporation of this reagent increased the yield of the product (naltrexone methobromide) to about 77.5% and decreased the side products to about 5.1%. Addition of HBr suppresses the ionization of the C(3) hydroxide (phenolic hydroxide) of naltrexone to form Nal (see Scheme 4) and thereby reduces the chemical reactivity of the C(3) hydroxide toward MeBr. Further, addition of a strong anhydrous acid (HBr) to the reaction system permits use of partially hydrated naltrexone (Naltrexone.2H2O) as a starting material instead of anhydrous naltrexone thereby eliminating the processing costs associated with dehydration of naltrexone. Since an additional reaction step is required to prepare anhydrous naltrexone from the hydrate (Naltrexone.2H2O), addition of HBr would reduce processing costs.

Quellen und Nachweise

ORD-Eintrag
ord-b558ea5a76c9408a93c7bef9dd734d30
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09415044B2

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