Hydrochloric Acid → (R)-Piperazine-2-carboxylic acid

HRID 1951280Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1951280
[OH-:1].[Na+].C([O:7]C(OC(OC(C)(C)C)=O)=O)(C)(C)C.[N:18]1C2C(=CC=CC=2S(Cl)(=O)=O)C=C[CH:19]=1.C([N:34]([CH2:37][CH3:38])[CH2:35][CH3:36])C.Cl>O1CCOCC1.O>[NH:34]1[CH2:35][CH2:36][NH:18][CH2:19][C@@H:37]1[C:38]([OH:7])=[O:1]

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 14798Sodium Hydroxide2×HCID 292208-Quinolinesulfonyl chlorideHCID 90495Di-tert-butyl dicarbonate

Produkt 1

HCID 6558437(R)-Piperazine-2-carboxylic acidAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 218864351,4-Dioxane--water (1/1)Lösungsmittel

Versuchsvorschrift

2CSA (9.492 g, 15.96 mmol) was dissolved in dioxane/water 1:1 (60 ml) and concentrated sodium hydroxide was added until the pH reached 9-10. Di-tert-butyl-dicarbonate (3.755 g, 17.55 mmol) was then added and the mixture was stirred 6 h at room temperature. A white precipitate appeared, the pH dropped to 7 and was brought back to 9 by the addition of concentrated NaOH. 8-quinoline sulfonylchloride (3.63 g, 15.64 mmol) and triethylamine (4.33 ml, 31.28 mmol) were slowly added and the mixture was stirred overnight at room temperature. The solution was made acidic by the addition of HCl 1N and the white precipitate thus obtained was filtered and dried to give the desired compound.

Aufarbeitung

  1. additionthe pH dropped to 7
  2. stirringthe mixture was stirred overnight at room temperature
  3. customthe white precipitate thus obtained
  4. filtrationwas filtered
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-18dae4225cdb497eb4a21ee615bd23ee
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08404690B2

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