Water → 2-(6-{(Naphthalene-2-sulfonyl)-[2-(2-oxopyrrolidin-1-yl)ethyl]amino}-3-azabicyclo[3.1.0]hex-3-yl)pyrimidine-5-carboxylic acid

HRID 2079790

Reaktionsgleichung

Reaktionsgleichung von HRID 2079790
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]([N:14]([CH2:32][CH2:33][N:34]1[CH2:38][CH2:37][CH2:36][C:35]1=[O:39])[CH:15]1[CH:20]2[CH:16]1[CH2:17][N:18]([C:21]1[N:26]=[CH:25][C:24]([C:27]([O:29]CC)=[O:28])=[CH:23][N:22]=1)[CH2:19]2)(=[O:13])=[O:12].[O-]CC.[Na+].Cl.NO.O>CCO>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]([N:14]([CH2:32][CH2:33][N:34]1[CH2:38][CH2:37][CH2:36][C:35]1=[O:39])[CH:15]1[CH:20]2[CH:16]1[CH2:17][N:18]([C:21]1[N:26]=[CH:25][C:24]([C:27]([OH:29])=[O:28])=[CH:23][N:22]=1)[CH2:19]2)(=[O:12])=[O:13]

Komponenten

6

Edukt 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 2723922Sodium ethoxideHCID 59367586Ethyl 2-(6-{(naphthalene-2-sulfonyl)-[2-(2-oxopyrrolidin-1-yl)ethyl]amino}-3-azabicyclo[3.1.0]hex-3-yl)pyrimidine-5-carboxylate

Produkt 1

HCID 593676352-(6-{(Naphthalene-2-sulfonyl)-[2-(2-oxopyrrolidin-1-yl)ethyl]amino}-3-azabicyclo[3.1.0]hex-3-yl)pyrimidine-5-carboxylic acidAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a solution of ethyl 2-(6-{(naphthalene-2-sulfonyl)-[2-(2-oxopyrrolidin-1-yl)ethyl]amino}-3-azabicyclo[3.1.0]hex-3-yl)pyrimidine-5-carboxylate (0.749 g, 1.4 mmol) in EtOH (8 ml) was added sodium ethoxide (1.08 g, 15.8 mmol) and hydroxylamine hydrochloride (1.30 g, 18.7 mmol). The mixture was stirred at 40° C. for 18 h, then water (20 ml) was added. The product was extracted with DCM (2×100 ml), and the combined organic extracts were dried (MgSO4) and concentrated in vacuo. The expected hydroxamate product was in fact proved not to have formed. The reaction yielded instead the acid. Purification by reverse phase HPLC yielded the title compound (232 mg, 32%). This was used directly in the next step without characterisation.

Aufarbeitung

  1. extractionThe product was extracted with DCM (2×100 ml)
  2. dry with materialthe combined organic extracts were dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customto have formed
  5. customThe reaction yielded instead the acid
  6. customPurification by reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-4c5f0e421843415b8249f550bea273fc
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07932246B2

Verknüpfte Notizen

Wird geladen…