Lithium Hydroxide → 3-Chloro-5-{[(2-hydroxyethyl)amino]carbonyl}-1H-pyrrole-2-carboxylic acid

HRID 1874965Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1874965
[Li+].[OH-].[Cl:3][C:4]1[CH:8]=[C:7]([C:9]([NH:11][CH2:12][CH2:13][OH:14])=[O:10])[NH:6][C:5]=1[C:15]([O:17]C)=[O:16]>C1COCC1.CO>[Cl:3][C:4]1[CH:8]=[C:7]([C:9]([NH:11][CH2:12][CH2:13][OH:14])=[O:10])[NH:6][C:5]=1[C:15]([OH:17])=[O:16]

Komponenten

5

Edukt 2

HCID 3939Lithium HydroxideHCID 68487232Methyl 3-chloro-5-{[(2-hydroxyethyl)amino]carbonyl}-1H-pyrrole-2-carboxylate

Produkt 1

HCID 684835273-Chloro-5-{[(2-hydroxyethyl)amino]carbonyl}-1H-pyrrole-2-carboxylic acidAusbeute 54,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

LiOH (2 mL, 2 mmol) was added to a solution of methyl 3-chloro-5-{[(2-hydroxyethyl)amino]carbonyl}-1H-pyrrole-2-carboxylate (0.082 g, 0.33 mmol) in THF (2 mL) and methanol (2 mL). The solution was stirred at RT overnight. The solvent was evaporated and the residue partitioned between EtOAc and 1 N HCl. The organic layer was separated, dried over MgSO4, filtered and evaporated to afford very little solid. The aqueous layer was evaporated to a residue and the salts extracted with methanol. The methanol was evaporated to afford the title compound (0.042 g, 54%). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.16 (br. s., 1H), 8.40 (t, 1H), 6.61-7.10 (m, 1H), 3.45 (t, 2H), 3.26 (q, 2H).

Aufarbeitung

  1. customThe solvent was evaporated
  2. customthe residue partitioned between EtOAc and 1 N HCl
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customto afford very little solid
  8. customThe aqueous layer was evaporated to a residue
  9. extractionthe salts extracted with methanol
  10. customThe methanol was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-d75fd0152b0f4dcf8f4f7d6c5770480b
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304419B2

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