Methanol → HCID 68283591, Verbindung

HRID 1527213Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1527213
C([O:5][C:6](=[O:21])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([Cl:17])=[CH:14][CH:15]=2)[C:10]([C:18](=[O:20])[NH2:19])=[CH:9]1)(C)(C)C.C(O)(C(F)(F)F)=O.CO>C(Cl)Cl>[C:18]([C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=2)[N:8]([CH2:7][C:6]([OH:21])=[O:5])[CH:9]=1)(=[O:20])[NH2:19]

Komponenten

5

Edukt 3

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 68283031(3-Carbamoyl-5-chloro-indol-1-yl)-acetic acid tert-butyl ester

Produkt 1

HCID 68283591HCID 68283591, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (3-carbamoyl-5-chloro-indol-1-yl)-acetic acid tert-butyl ester (455 mg, 0.973 mmol) in CH2Cl2 (6.0 mL) was added TFA (3.0 mL) at RT and stirring was continued for 2 h. Methanol was then added to the reaction mixture and volatiles were removed in vacuo. The residue was taken up in methanol and concentrated again under reduced pressure. The residue was dissolved in 1N aqueous NaOH and washed with CH2Cl2 (3×). The water phase was acidified to pH 2 by adding 6N aqueous HCl to form a white suspension. The precipitate was filtered off, washed with water and dried in vacuo to afford the crude title compound as a white solid. MS (LC/MS): 253 [M+H]+, 505 [2M+H]+; tR (HPLC conditions b): 3.99 min. The product was used in the next reaction step without further purification.

Aufarbeitung

  1. customwere removed in vacuo
  2. concentrationconcentrated again under reduced pressure
  3. dissolutionThe residue was dissolved in 1N aqueous NaOH
  4. washwashed with CH2Cl2 (3×)
  5. additionby adding 6N aqueous HCl
  6. customto form a white suspension
  7. filtrationThe precipitate was filtered off
  8. washwashed with water
  9. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-aa73ffd7f8cd4ceeb5a65088f4d63610
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09085555B2

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