Hydrochloric Acid → HCID 19787897, Verbindung

HRID 1656506Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1656506
[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:17](=[O:18])[N:16]([CH2:19][C:20]([NH:22][CH:23]([CH:30]([CH3:32])[CH3:31])[CH:24]([OH:29])[C:25]([F:28])([F:27])[F:26])=[O:21])[C:15]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[N:14][CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C(C)=CC=CC=1C.FC(F)(F)S(O[Si:53]([C:56]([CH3:59])([CH3:58])[CH3:57])([CH3:55])[CH3:54])(=O)=O.Cl>ClCCl>[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:17](=[O:18])[N:16]([CH2:19][C:20]([NH:22][CH:23]([CH:30]([CH3:32])[CH3:31])[CH:24]([O:29][Si:53]([C:56]([CH3:59])([CH3:58])[CH3:57])([CH3:55])[CH3:54])[C:25]([F:27])([F:28])[F:26])=[O:21])[C:15]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)=[N:14][CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 79372,6-LutidineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 19787883HCID 19787883, Verbindung

Produkt 1

HCID 19787897HCID 19787897, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a suspension of 2-(5-benzyloxycarbonylamino-6-oxo-2-phenyl-1,6-dihydro-1-pyrimidinyl)-N-(3,3,3-trifluoro-2-hydroxy-1-isopropylpropyl)acetamide (1.13 g) and 2,6-lutidine (0.5 mL) in dichloromethane (5 mL) at 0° C. was added tert-butyldimethylsilyl trifluoromethanesulfonate (0.73 mL). The mixture was allowed to stir for 1.5 h. over which time the suspension became a solution. The mixture was poured into 1N hydrochloric acid and extracted into ether. The organic layer was washed (water), dried and evaporated to give an oil, which crystallized upon addition of ether:hexane to give a white solid. The solid was collected and washed with hexane to yield 2-(5-benzyloxycarbonylamino-6-oxo-2-phenyl-1,6-dihydro-1-pyrimidinyl)-N-(2-tert-butyldimethylsilyloxy-3,3,3-trifluoro-1-isopropylpropyl)acetamide as a white solid (1.1 g); MS: m/z=647(M+1).

Aufarbeitung

  1. extractionextracted into ether
  2. washThe organic layer was washed (water)
  3. customdried
  4. customevaporated
  5. customto give an oil, which
  6. customcrystallized upon addition of ether
  7. customhexane to give a white solid
  8. customThe solid was collected
  9. washwashed with hexane

Quellen und Nachweise

ORD-Eintrag
ord-09e034ab4e064bb69dc640ae85f6b960
Quelldatensatz
uspto-grants-1993_10
Patentnummer
US05254558

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