Diisopropylethylamine → 3-(benzyloxy)-5-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-N-(5-methyl-1,3-thiazol-2-yl)benzamide

HRID 20565

Reaktionsgleichung

Reaktionsgleichung von HRID 20565
CCN(C(C)C)C(C)C.[C:10]1([CH2:16][O:17][C:18]2[CH:19]=[C:20]([CH:24]=[C:25]([O:27][C@@H:28]([CH3:38])[CH2:29][O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])[CH:26]=2)[C:21]([OH:23])=O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:63][C:64]1[S:65][C:66]([CH3:69])=[CH:67][N:68]=1>CN(C=O)C>[CH2:16]([O:17][C:18]1[CH:19]=[C:20]([CH:24]=[C:25]([O:27][C@@H:28]([CH3:38])[CH2:29][O:30][Si:31]([C:34]([CH3:36])([CH3:37])[CH3:35])([CH3:32])[CH3:33])[CH:26]=1)[C:21]([NH:63][C:64]1[S:65][C:66]([CH3:69])=[CH:67][N:68]=1)=[O:23])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 3517702-Amino-5-methylthiazoleHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 536296343-[((1S)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-methylethyl)oxy]-5-[(phenylmethyl)oxy]benzoic acid

Produkt 1

HCID 593469333-(benzyloxy)-5-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-N-(5-methyl-1,3-thiazol-2-yl)benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

DIPEA (7.5 mL) was added to a suspension of 3-{(phenylmethyl)oxy}-5-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)benzoic acid (4.5 g, 0.011 mol), HATU (8.6 g, 0.023 mol) and 2-amino-5-methylthiazole (2.46 g, 0.022 mol) in DMF (70 mL). The resulting mixture was stirred at ambient temperature for 72 hours. The DMF was removed in vacuo. Water (100 mL) was added and the mixture extracted with ethyl acetate (3×50 mL). The extracts were combined and washed with brine (100 mL). The solution was dried (MgSO4), filtered, and evaporated in vacuo to give the crude product which was chromatographed on silica, eluting with a gradient of 50-100% ethyl acetate in isohexane, to give the desired compound. (1.7 g).

Aufarbeitung

  1. customThe DMF was removed in vacuo
  2. additionWater (100 mL) was added
  3. extractionthe mixture extracted with ethyl acetate (3×50 mL)
  4. washwashed with brine (100 mL)
  5. dry with materialThe solution was dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customto give the crude product which
  9. customwas chromatographed on silica
  10. washeluting with a gradient of 50-100% ethyl acetate in isohexane

Quellen und Nachweise

ORD-Eintrag
ord-51c3d8d5755b4a798dcbc43b60381424
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745475B2

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