Ammonium formate → Compound 18

HRID 722402Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 722402
C([O:8][C:9]1[CH:10]=[CH:11][C:12]2[O:17][C@@H:16]([C:18]3[CH:32]=[CH:31][C:21]([O:22][CH2:23][C@@H:24]([N:26]4[CH2:30][CH2:29][CH2:28][CH2:27]4)[CH3:25])=[CH:20][CH:19]=3)[C@@H:15]([C:33]3[CH:38]=[CH:37][C:36]([O:39][Si](C(C)C)(C(C)C)C(C)C)=[CH:35][CH:34]=3)[S:14][C:13]=2[CH:50]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CCO.CCOC(C)=O.O.[Pd]>[OH:39][C:36]1[CH:37]=[CH:38][C:33]([C@H:15]2[S:14][C:13]3[CH:50]=[C:9]([OH:8])[CH:10]=[CH:11][C:12]=3[O:17][C@H:16]2[C:18]2[CH:32]=[CH:31][C:21]([O:22][CH2:23][C@@H:24]([N:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)[CH3:25])=[CH:20][CH:19]=2)=[CH:34][CH:35]=1

Komponenten

5

Edukt 2

HCID 2723923Ammonium formateHCID 587430611-{(1S)-2-[4-((2S,3R)-6-(benzyloxy)-3-{4-[(triisopropylsilyl)oxy]phenyl}-2,3-dihydro-1,4-benzoxathiin-2-yl)phenoxy]-1-methylethyl}pyrolidine

Produkt 1

HCID 449208Compound 18

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 86601158Ethanol ethyl acetate waterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A stirred mixture of 102 mg (0.14 mmol) of compound 10a, generated in Example 10, Step A, 30.6 mg (0.29 mmol) of palladium black and 181.2 mg (0.29 mmol) ammonium formate in 3 mL of EtOH/EtOAc/H2O (7:2:1) was heated at 80° C. for 2 h. The reaction mixture was filtered through a pad of Celite® to remove the catalyst, washed thoroughly with EtOH/EtOAc/H2O (7:2:1), and the filtrate was partitioned between water and EtOAc. The organic phase was separated, dried over Na2SO4, filtered, evaporated, and dried in vacuo to give the crude product which was used without purification.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through a pad of Celite®
  2. customto remove the catalyst
  3. washwashed thoroughly with EtOH/EtOAc/H2O (7:2:1)
  4. customthe filtrate was partitioned between water and EtOAc
  5. customThe organic phase was separated
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1ce3b14e8f5048ebb4648f2a35f88b26
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07138426B2

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