Sodium Carbonate → HCID 178513418, Verbindung

HRID 1267849Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1267849
[C:1]([C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])#[N:2].Cl.[NH2:19][OH:20].C([O-])([O-])=O.[Na+].[Na+]>C(O)C.O>[OH:20][NH:19][C:1]([C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])=[NH:2]

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 11535955(S)-1-N-Cbz-2-cyano-pyrrolidine

Produkt 1

HCID 178513418HCID 178513418, VerbindungAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Part A. Benzyl (S)-2-cyanopyrrolidine-1-carboxylate (500 mg, 2.17 mmol) was dissolved in aqueous ethanol (3 mL) and water (1 mL). Hydroxylamine hydrochloride (152 mg, 2.17 mmol) and Na2CO3 (115 mg, 1.08 mmol) were added and the reaction mixture heated to 100° C. for 1 h. The ethanol was removed and the aqueous residue was extracted with dichloromethane (3×25 mL), dried over Na2SO4 decanted and concentrated yielding benzyl (S)-2-(N-hydroxycarbamimidoyl)pyrrolidine-1-carboxylate as a pale yellow gum (428 mg, 75% yield): HPLC (method 1) tR=1.40 min, Purity 76%; LCMS (method 4) tR=0.81 min, m/z 264 (M+H).

Aufarbeitung

  1. customThe ethanol was removed
  2. extractionthe aqueous residue was extracted with dichloromethane (3×25 mL)
  3. dry with materialdried over Na2SO4
  4. customdecanted
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-1f99292536a042108e8e325c4a8158e4
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06555542B1

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