Tetrahydrofuran → (R)-3-(5-Methyl-3-oxo-1H-pyrrolo[1,2-c]imidazol-2(3H)-yl)-2,3-dihydro-1H-indene-5-carboxylic acid

HRID 1253663Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1253663
C[O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH2:10][C@H:11]2[NH:14][CH2:15][C:16]2[N:17]([C:21](OC(C)(C)C)=[O:22])[CH:18]=[CH:19][CH:20]=2)=[CH:7][CH:6]=1)=[O:4].[H-].[Na+].[CH2:30]1COCC1>>[CH3:30][C:18]1[N:17]2[C:21](=[O:22])[N:14]([C@H:11]3[C:12]4[C:8](=[CH:7][CH:6]=[C:5]([C:3]([OH:2])=[O:4])[CH:13]=4)[CH2:9][CH2:10]3)[CH2:15][C:16]2=[CH:20][CH:19]=1

Komponenten

4

Edukt 3

HCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 59505448(R)-tert-butyl 2-((6-(methoxycarbonyl)-2,3-dihydro-1H-inden-1-ylamino)methyl)-1H-pyrrole-1-carboxylate

Produkt 1

HCID 59505195(R)-3-(5-Methyl-3-oxo-1H-pyrrolo[1,2-c]imidazol-2(3H)-yl)-2,3-dihydro-1H-indene-5-carboxylic acidAusbeute 26 %

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

A solution of (R)-tert-butyl 2-((6-(methoxycarbonyl)-2,3-dihydro-1H-inden-1-ylamino)methyl)-1H-pyrrole-1-carboxylate (500 mg, 1.3 mmol, 1.0 eq.) in THF (5 ml) was added to a stirred suspension of NaH (104 mg, 2.6 mmol, 2.0 eq., 60% in mineral oil) in THF (15 ml) at 0° C. and the resulting reaction mixture was stirred at 25° C. for 14 h. The reaction mixture was quenched with water (50 ml) and washed with ethyl acetate (50 ml). The aqueous layer was acidified with 2 N HCl (5 ml) and extracted with ethyl acetate (2×100 ml). The combined organic fractions were washed with brine (50 ml), dried over sodium sulfate and the solvent evaporated under reduced pressure. The residue obtained was used for the next step without further purification. Yield: 26% (100 mg, 0.34 mmol).

Aufarbeitung

  1. customthe resulting reaction mixture
  2. customThe reaction mixture was quenched with water (50 ml)
  3. washwashed with ethyl acetate (50 ml)
  4. extractionextracted with ethyl acetate (2×100 ml)
  5. washThe combined organic fractions were washed with brine (50 ml)
  6. dry with materialdried over sodium sulfate
  7. customthe solvent evaporated under reduced pressure
  8. customThe residue obtained
  9. customwas used for the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-d4cc32dd4c7246f0ae20a670a4b8552b
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08455475B2

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