Perchloric Acid → HCID 86691589, Verbindung

HRID 1468745Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1468745
[CH2:1]([O:3][C:4](=[O:23])[C@H:5]([C:7]1[C:8]([CH3:22])=[N:9][C:10]2[N:11]([N:14]=[C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:16]=2)[C:12]=1[I:13])[OH:6])[CH3:2].Cl(O)(=O)(=O)=O>C(Cl)Cl.C(OC(C)(C)C)(=O)C>[C:7]([O:6][C@@H:5]([C:7]1[C:8]([CH3:22])=[N:9][C:10]2[N:11]([N:14]=[C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:16]=2)[C:12]=1[I:13])[C:4]([O:3][CH2:1][CH3:2])=[O:23])([CH3:8])([CH3:12])[CH3:5]

Komponenten

5

Edukt 2

HCID 24247Perchloric AcidHCID 86691588(S)-ethyl 6-(2-ethoxy-1-hydroxy-2-oxoethyl)-7-iodo-5-methylpyrazolo[1,5-a]pyrimidine-2-carboxylate

Produkt 1

HCID 86691589HCID 86691589, VerbindungAusbeute 135,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 10908tert-Butyl acetateLösungsmittel

Versuchsvorschrift

To a stirred solution of (S)-ethyl 6-(2-ethoxy-1-hydroxy-2-oxoethyl)-7-iodo-5-methylpyrazolo[1,5-a]pyrimidine-2-carboxylate (5.3 g, 12.2 mmol) in CH2Cl2 (150 mL) and t-butyl acetate (105 mL) at rt was added perchloric acid (3.15 mL, 36.7 mmol). The reaction flask was sealed. After stirring for 3 h, the reaction mixture was diluted with CH2Cl2 (100 mL), carefully quenched with sat. aq. NaHCO3 (50 mL). The organic layer was separated and washed with brine (100 mL), dried (Na2SO4), filtered and concentrated in vacuo to give a yellow liquid. This crude product was purified by flash column chromatography on a silica gel column using (10-50% EtOAc/Hex as eluant) to afford the desired (S)-ethyl 6-(1-(tert-butoxy)-2-ethoxy-2-oxoethyl)-7-iodo-5-methylpyrazolo[1,5-a]pyrimidine-2-carboxylate (4.5 g, 8.28 mmol, 67.7% yield) as viscous oil. In addition, 700 mg of starting material was recovered. 1H NMR (500 MHz, CDCl3) δ 7.31 (s, 1H), 5.56 (s, 1H), 4.51 (q, J=7.1 Hz, 2H), 4.26-4.16 (m, 2H), 2.71 (s, 3H), 1.48 (t, J=7.2 Hz, 3H), 1.30 (s, 9H), 1.23 (t, J=7.0 Hz, 3H). LCMS (M+H)=490.0.

Aufarbeitung

  1. customThe reaction flask was sealed
  2. customcarefully quenched with sat. aq. NaHCO3 (50 mL)
  3. customThe organic layer was separated
  4. washwashed with brine (100 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a yellow liquid
  9. customThis crude product was purified by flash column chromatography on a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-fb900eccbc784f61b910508352204d38
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09006235B2

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