Dimethyl Sulfoxide → (2s)-n-{(1s,3s,4s)-1-Benzyl-4-{[(2,6-dimethylphenoxy)acetyl]amino}-3-[(methylthio)methoxy]-5-phenylpentyl}-3-methyl-2-(2-oxotetrahydropyrimidin-1(2h)-yl)butanamide

HRID 1968905Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1968905
[CH2:1]([C@H:8]([NH:33][C:34](=[O:46])[C@@H:35]([N:39]1[CH2:44][CH2:43][CH2:42][NH:41][C:40]1=[O:45])[CH:36]([CH3:38])[CH3:37])[CH2:9][C@H:10]([OH:32])[C@@H:11]([NH:19][C:20](=[O:31])[CH2:21][O:22][C:23]1[C:28]([CH3:29])=[CH:27][CH:26]=[CH:25][C:24]=1[CH3:30])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:47][S:48]([CH3:50])=O.C(OC(=O)C)(=O)C>C(O)(=O)C>[CH2:1]([C@H:8]([NH:33][C:34](=[O:46])[C@@H:35]([N:39]1[CH2:44][CH2:43][CH2:42][NH:41][C:40]1=[O:45])[CH:36]([CH3:38])[CH3:37])[CH2:9][C@H:10]([O:32][CH2:47][S:48][CH3:50])[C@@H:11]([NH:19][C:20](=[O:31])[CH2:21][O:22][C:23]1[C:24]([CH3:30])=[CH:25][CH:26]=[CH:27][C:28]=1[CH3:29])[CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 679Dimethyl SulfoxideHCID 7918Acetic AnhydrideHCID 92727Lopinavir

Produkt 1

HCID 42638008(2s)-n-{(1s,3s,4s)-1-Benzyl-4-{[(2,6-dimethylphenoxy)acetyl]amino}-3-[(methylthio)methoxy]-5-phenylpentyl}-3-methyl-2-(2-oxotetrahydropyrimidin-1(2h)-yl)butanamideAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a solution of the compound of Example 3 (3.0 g, 4.8 mmol), DMSO (18 mL), and acetic acid (3.6 mL) at room temperature was added acetic anhydride (23 mL), and the reaction was stirred for 48 hours at room temperature. The reaction was quenched with ice and 10% Na2CO3 was added to adjust the pH to 7. The mixture was extracted with ethyl acetate and washed with 10% Na2CO3 and brine. The organic was dried over Na2SO4, filtered and evaporated to give the crude product, which was chromatographed on silica gel eluting first with 25-100% ethyl acetate in dichloromethane to give the title compound (2.1 g, 64% yield).

Aufarbeitung

  1. customThe reaction was quenched with ice and 10% Na2CO3
  2. additionwas added
  3. extractionThe mixture was extracted with ethyl acetate
  4. washwashed with 10% Na2CO3 and brine
  5. dry with materialThe organic was dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customto give the crude product, which
  9. customwas chromatographed on silica gel eluting first with 25-100% ethyl acetate in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-78770417e7674de5a6b5651ef92c1437
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08426388B2

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