Triethylamine → (2s)-n-{(1s,3s,4s)-1-Benzyl-4-{[(2,6-dimethylphenoxy)acetyl]amino}-3-[1-(ethylthio)ethoxy]-5-phenylpentyl}-3-methyl-2-(2-oxotetrahydropyrimidin-1(2h)-yl)butanamide

HRID 1968907Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1968907
ClN1C(=O)CCC1=O.[CH2:9]([S:11][CH2:12][CH3:13])[CH3:10].[CH2:14]([C@H:21]([NH:46][C:47](=[O:59])[C@@H:48]([N:52]1[CH2:57][CH2:56][CH2:55][NH:54][C:53]1=[O:58])[CH:49]([CH3:51])[CH3:50])[CH2:22][C@H:23]([OH:45])[C@@H:24]([NH:32][C:33](=[O:44])[CH2:34][O:35][C:36]1[C:41]([CH3:42])=[CH:40][CH:39]=[CH:38][C:37]=1[CH3:43])[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C>O1CCCC1>[CH2:14]([C@H:21]([NH:46][C:47](=[O:59])[C@@H:48]([N:52]1[CH2:57][CH2:56][CH2:55][NH:54][C:53]1=[O:58])[CH:49]([CH3:51])[CH3:50])[CH2:22][C@H:23]([O:45][CH:9]([S:11][CH2:12][CH3:13])[CH3:10])[C@@H:24]([NH:32][C:33](=[O:44])[CH2:34][O:35][C:36]1[C:37]([CH3:43])=[CH:38][CH:39]=[CH:40][C:41]=1[CH3:42])[CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 9609Ethyl sulfideHCID 31398ChlorosuccinimideHCID 92727Lopinavir

Produkt 1

HCID 42637794(2s)-n-{(1s,3s,4s)-1-Benzyl-4-{[(2,6-dimethylphenoxy)acetyl]amino}-3-[1-(ethylthio)ethoxy]-5-phenylpentyl}-3-methyl-2-(2-oxotetrahydropyrimidin-1(2h)-yl)butanamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

A slurry of N-chlorosuccinimide (6.5 g, 48.7 mmol) in tetrahydrofuran (50 mL) was cooled to −10° C., followed by addition of diethyl sulfide (7.0 mL) and then by addition of a solution of Example 3 (5.0 g) in tetrahydrofuran (20 mL). A solution of triethylamine (9.0 mL) in tetrahydrofuran (15 mL) was then added dropwise and the mixture was stirred at −10° C. for 1.5 h. The reaction was quenched with 10% Na2CO3 and extracted twice with ethyl acetate. The combined organic was washed with water and brine and dried over MgSO4, filtered and evaporated to give the crude product (7.5 g).

Aufarbeitung

  1. customThe reaction was quenched with 10% Na2CO3
  2. extractionextracted twice with ethyl acetate
  3. washThe combined organic was washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-71fe7e6af3c44cf08de9c42c89a8c1f1
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08426388B2

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