Ammonium Chloride → HCID 19787913, Verbindung

HRID 1656509Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1656509
[C:1]([NH:4][C:5]1[C:10](=[O:11])[N:9]([CH2:12][C:13]([NH:15][CH:16]([CH:30]([CH3:32])[CH3:31])[CH:17]([O:22][Si](C(C)(C)C)(C)C)[C:18]([F:21])([F:20])[F:19])=[O:14])[C:8]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[N:7][CH:6]=1)(=[O:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[NH4+]>O1CCCC1>[C:1]([NH:4][C:5]1[C:10](=[O:11])[N:9]([CH2:12][C:13]([NH:15][CH:16]([CH:30]([CH3:31])[CH3:32])[CH:17]([OH:22])[C:18]([F:20])([F:21])[F:19])=[O:14])[C:8]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[N:7][CH:6]=1)(=[O:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 19787874HCID 19787874, Verbindung

Produkt 1

HCID 19787913HCID 19787913, VerbindungAusbeute 87,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2-(5-acetamido-6-oxo-2-phenyl-1,6-dihydro-1-pyrimidinyl)-N-(2-tert-butyldimethylsilyloxy-3,3,3-trifluoro-1-isopropylpropyl)acetamide (0.86 g) in tetrahydrofuran (15 mL) at 0° C. was added tetrabutylammonium fluoride (1.95 mL, 1M in tetrahydrofuran) and the resulting solution was allowed to stir for 5 min. The mixture was poured into saturated aqueous ammonium chloride and the product extracted into ethyl acetate. The organic solution was washed (water), dried, and evaporated. The resulting white solid was collected and washed with ether:hexane to provide 2-(5-acetamido-6-oxo-2-phenyl-1,6-dihydro-1-pyrimidinyl)-N-(3,3,3-trifluoro-1-isopropyl-2-hydroxypropyl)acetamide (0.6 g); NMR: 8.87 (s,1), 8.07 (d,1), 7.57 (m,5), 4.62 (d,1), 4.42 (d,1), 4.10 (m,1), 3.68 (t,1), 2.18 (s,3), 1.80 (m,1), 0.89 (d,3), 0.82 (d,3).

Aufarbeitung

  1. extractionthe product extracted into ethyl acetate
  2. washThe organic solution was washed (water)
  3. customdried
  4. customevaporated
  5. customThe resulting white solid was collected
  6. washwashed with ether

Quellen und Nachweise

ORD-Eintrag
ord-5a0cd7e0a8e4419993e4bb4f57cd1502
Quelldatensatz
uspto-grants-1993_10
Patentnummer
US05254558

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