Perchloric Acid → HCID 86691589, Verbindung

HRID 1630309Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1630309
[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 135,4 %

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, 12.23 mmol) in CH2Cl2 (150 mL) and t-butyl acetate (105 mL) was added perchloric acid (3.15 mL, 36.7 mmol) at rt and sealed the reaction flask. After 3 h, the reaction mixture was diluted with CH2Cl2 (100 mL), carefully quenched with sat. NaHCO3 (50 mL), organic layer separated and washed with brine (100 mL), dried (Na2SO4), filtered and concentrated to give yellow liquid. This was purified by flash column chromatography on 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. 700 mg of starting material was also 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. customsealed the reaction flask
  2. customcarefully quenched with sat. NaHCO3 (50 mL), organic layer
  3. customseparated
  4. washwashed with brine (100 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give yellow liquid
  9. customThis was purified by flash column chromatography on silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-059e92ba39a64dd1b4749c676a265e43
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08791108B2

Notizen zur Reaktion

Wird geladen…