Diisopropylethylamine → N-[(1S,2S,4R)-1-Benzyl-4-(3,3-dimethyl-butylcarbamoyl)-2-hydroxypenty]-3,5-bis-(2-oxo-pyrrolidin-1-yl)benzamide

HRID 1612478Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1612478
[CH3:1][C:2]([CH3:23])([CH3:22])[CH2:3][CH2:4][NH:5][C:6](=[O:21])[C@H:7]([CH3:20])[CH2:8][C@H:9]([OH:19])[C@@H:10]([NH2:18])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CCN(C(C)C)C(C)C.[O:33]=[C:34]1[CH2:38][CH2:37][CH2:36][N:35]1[C:39]1[CH:40]=[C:41]([CH:45]=[C:46]([N:48]2[CH2:52][CH2:51][CH2:50][C:49]2=[O:53])[CH:47]=1)[C:42](O)=[O:43].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH2:11]([C@H:10]([NH:18][C:42](=[O:43])[C:41]1[CH:40]=[C:39]([N:35]2[CH2:36][CH2:37][CH2:38][C:34]2=[O:33])[CH:47]=[C:46]([N:48]2[CH2:52][CH2:51][CH2:50][C:49]2=[O:53])[CH:45]=1)[C@@H:9]([OH:19])[CH2:8][C@H:7]([C:6](=[O:21])[NH:5][CH2:4][CH2:3][C:2]([CH3:22])([CH3:1])[CH3:23])[CH3:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 111620233,5-bis(2-oxopyrrolidin-1-yl)benzoic AcidHCID 68890142(2R,4S,5S)-5-amino-4-hydroxy-2-methyl-6-phenylhexanoic acid (3,3-dimethylbutyl)-amide

Produkt 1

HCID 10196800N-[(1S,2S,4R)-1-Benzyl-4-(3,3-dimethyl-butylcarbamoyl)-2-hydroxypenty]-3,5-bis-(2-oxo-pyrrolidin-1-yl)benzamideAusbeute 64,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of (2R,4S,5S)-5-amino-4-hydroxy-2-methyl-6-phenylhexanoic acid (3,3-dimethylbutyl)amide (D2) (46 mg, 0.145 mmol) in DMF (2 ml) was added iPr2NEt (61 μl, 0.348 mmol) followed by 3,5-bis-2-oxopyrrolidin-1-yl)benzoic acid (D8) (50 mg, 0.174 mmol) and HATU (77 mg, 0.203 mmol). The reaction mixture was stirred at room temperature for 6 hours. The solvent was evaporated to dryness and the residue was partitioned between 0.5 M HCl and DCM. The organic phase was separated and washed with NaHCO3, brine and dried over MgSO4, filtered and evaporated to afford the crude product (61 mg) as yellow oil. The product was triturated in petroleum/diethylether which yielded E5 (55 mg) as a yellow solid.

Aufarbeitung

  1. customThe solvent was evaporated to dryness
  2. customthe residue was partitioned between 0.5 M HCl and DCM
  3. customThe organic phase was separated
  4. washwashed with NaHCO3, brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customto afford the crude product (61 mg) as yellow oil
  9. customThe product was triturated in petroleum/diethylether which

Quellen und Nachweise

ORD-Eintrag
ord-0c83f70b4df6449f8907273222652b61
Quelldatensatz
uspto-grants-2006_01
Patentnummer
US06992103B2

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