Diisopropylethylamine → HCID 58432115, Verbindung

HRID 512624Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 512624
Cl[CH2:2][CH2:3][CH2:4][S:5]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([O:20][CH3:21])[C:16]([O:18][CH3:19])=[O:17])=[CH:11][CH:10]=1)(=[O:7])=[O:6].C(N(CC)C(C)C)(C)C>CN(C=O)C.O.Cl.[Cl-].[Na+].O>[O:6]=[S:5]1(=[O:7])[CH2:4][CH2:3][CH2:2][N:8]1[C:9]1[CH:14]=[CH:13][C:12]([CH:15]([O:20][CH3:21])[C:16]([O:18][CH3:19])=[O:17])=[CH:11][CH:10]=1

Komponenten

7

Edukt 2

HCID 81531DiisopropylethylamineHCID 58432097Methyl 2-(4-(3-chloropropylsulfonamido)phenyl)-2-methoxyacetate

Produkt 1

HCID 58432115HCID 58432115, VerbindungAusbeute 75,1 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 313Hydrochloric AcidLösungsmittelHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of methyl 2-(4-(3-chloropropylsulfonamido)phenyl)-2-methoxyacetate (1.03 g, 3.07 mmol) in anhydr DMF (10 mL) was added N,N-diisopropylethylamine (2.0 mL, 11.5 mmol). The mixture was heated at 50° C. under argon for 17 hrs. After cooling to room temperature, the reaction was diluted with H2O, 1 M HCl and brine then extracted with EtOAc. The combined organics were washed with 1 M HCl, H2O and brine the dried over Na2SO4 and concentrated in vacuo. The residue was triturated with Et2O-EtOAc. After sitting overnight, the solution was decanted from solids then concentrated in vacuo. Purification by chromatography (50-70% EtOAc-hexanes) provided methyl 2-(4-(1,1-dioxidoisothiazolidin-2-yl)phenyl)-2-methoxyacetate as an impure oil (0.69 g, 75% yield). The product was used in the next synthetic step without further purification.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. extractionthen extracted with EtOAc
  3. washThe combined organics were washed with 1 M HCl, H2O and brine the
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated with Et2O-EtOAc
  7. customthe solution was decanted from solids
  8. concentrationthen concentrated in vacuo
  9. customPurification by chromatography (50-70% EtOAc-hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-90d1fd1531cd42d1bc005be44d3ffa05
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09102643B2

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