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Hydrochloric Acid → (3Z)-2,6-diamino-2-methylhex-3-enoic Acid Dihydrochloride

HRID 2306884
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2306884
[ClH:1].[NH2:2][C:3]([CH3:12])(/[CH:7]=[CH:8]\[CH2:9][C:10]#[N:11])[C:4]([OH:6])=[O:5].[BH4-].[Na+].Cl>CO>[ClH:1].[ClH:1].[NH2:2][C:3]([CH3:12])(/[CH:7]=[CH:8]\[CH2:9][CH2:10][NH2:11])[C:4]([OH:6])=[O:5]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 9942357(3Z)-2-amino-5-cyano-2-methylpent-3-enoic Acid Hydrochloride

Produkt 1

HCID 9813377(3Z)-2,6-diamino-2-methylhex-3-enoic Acid Dihydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

The (3Z)-2-amino-5-cyano-2-methylpent-3-enoic acid hydrochloride product of Example 1k is taken up in MeOH. To this is added Co(II)Cl2.6H2O in one portion with stirring under argon during which the reaction mixture is expected to turn purple. This is followed by the cautious addition of NaBH4 in 6 portions over 15 min. at 25° C. during which the reaction mixture is expected to turn black. HCl is then added carefully and the reaction mixture is stirred until the reaction becomes a light purple color. It is then concentrated under reduced pressure and the residue is subjected to BioRad ‘H’ form ion exchange resin. Elution with 1% NH4OH/H2O gives the desired fraction. This is concentrated to drive off excess NH3 at <55° C. on a rotary evaporator and then acidified to pH 4.5 with conc. HCl before it is concentrated to dryness to afford the desired title product.

Aufarbeitung

  1. stirringthe reaction mixture is stirred until the reaction
  2. concentrationIt is then concentrated under reduced pressure
  3. washElution with 1% NH4OH/H2O
  4. customgives the desired fraction
  5. concentrationThis is concentrated
  6. customat <55° C.
  7. customon a rotary evaporator
  8. concentrationis concentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-fb317b16735e40cc83dfde129a81191e
Quelldatensatz
uspto-grants-2004_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06828456B2

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