Dichloromethane → HCID 59314165, Verbindung

HRID 1047909Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1047909
[NH2:1][C:2]1([C:11]([OH:13])=[O:12])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3]1.C(Cl)Cl.[CH3:17][CH2:18]N(C(C)C)C(C)C.[F:26][C:27]1([F:39])[O:31][C:30]2[CH:32]=[CH:33][CH:34]=[C:35]([C:36](Cl)=[O:37])[C:29]=2[O:28]1>CN(C)C1C=CN=CC=1.CC(O)C.C(Cl)Cl>[CH2:17]([O:12][C:11]([C:2]1([NH:1][C:36]([C:35]2[C:29]3[O:28][C:27]([F:39])([F:26])[O:31][C:30]=3[CH:32]=[CH:33][CH:34]=2)=[O:37])[CH2:3][C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:10]1)=[O:13])[CH3:18]

Komponenten

7

Edukt 4

HCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 2509362-Aminoindane-2-carboxylic acidHCID 27740622,2-Difluoro-1,3-benzodioxole-4-carbonyl chloride

Produkt 1

HCID 59314165HCID 59314165, VerbindungAusbeute 112,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 21966342Isopropanol methylene chlorideLösungsmittel

Versuchsvorschrift

A 100 mL round bottom flask is charged with 2-aminoindan-2-carboxylic acid (340 mg, 1.66 mmol) and dry DCM (6 mL). A stirring bar is added and stirring is initiated. DIPEA (0.46 mL, 2.65 mmol) is added. 2-[(2,2-difluoro-benzo[1,3]dioxole-4-carbonyl chloride (438 mg, 1.99 mmol) is added. 4-Dimethylaminopyridine ([MFCD0006418], 2 mg, cat.) is added. The reaction is capped. After 18 days, tlc analysis (silica, 5% iPrOH/DCM) indicates that the starting is completely consumed. The contents of the reaction flask are transferred to a reparatory funnel and diluted with EtOAc (60 mL). This is washed with dilute aqueous HCl (2×25 mL), saturated aqueous NaHCO3 (2×25 mL), and brine (25 mL), dried over MgSO4, filtered and evaporated by pumping to constant weight to yield 0.73 g of dark brown foam. This is diluted with DCM and applied to a silica column (40 g) on an ISCO Companion. The column is eluted with 3 column volumes of 10% EtOAc-heptanes followed by a linear gradient to 50% EtOAc/heptanes over 10 Column Volumes. And then 90% EtOAc/heptanes for 2 Column Volumes. 17 mL fractions of UV positive eluent are collected. Fraction 8-10 are combined and evaporated by pumping to constant weight to give light orange solid (0.57 g, 88%).

Aufarbeitung

  1. additionA stirring bar is added
  2. customThe reaction is capped
  3. customis completely consumed
  4. customThe contents of the reaction flask are transferred to a reparatory funnel
  5. additiondiluted with EtOAc (60 mL)
  6. washThis is washed with dilute aqueous HCl (2×25 mL), saturated aqueous NaHCO3 (2×25 mL), and brine (25 mL)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-cfd98ba10e20437c9a52c5a45e306c2e
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569535B2

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