1,2-Dichloroethane → N1-{(1S,2R)-1-Benzyl-2-hydroxy-3-[(3-methoxybenzyl)amino]propyl)-N3,N3-dipropyl-1,3,5-benzenetricarboxamide

HRID 14014

Reaktionsgleichung

Reaktionsgleichung von HRID 14014
[NH2:1][C:2]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([C:13]([N:15]([CH2:19][CH2:20][CH3:21])[CH2:16][CH2:17][CH3:18])=[O:14])[CH:12]=1)[C:7](O)=[O:8])=[O:3].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.FC(F)(F)C(O)=O.[NH2:50][C@@H:51]([CH2:65][C:66]1[CH:71]=[C:70](F)[CH:69]=[C:68](F)[CH:67]=1)[C@H:52]([OH:64])[CH2:53][NH:54][CH2:55][C:56]1[CH:61]=[CH:60][CH:59]=[C:58]([O:62][CH3:63])[CH:57]=1>CN(C=O)C>[CH2:65]([C@H:51]([NH:50][C:7]([C:6]1[CH:5]=[C:4]([C:2]([NH2:1])=[O:3])[CH:12]=[C:11]([C:13]([N:15]([CH2:19][CH2:20][CH3:21])[CH2:16][CH2:17][CH3:18])=[O:14])[CH:10]=1)=[O:8])[C@H:52]([OH:64])[CH2:53][NH:54][CH2:55][C:56]1[CH:61]=[CH:60][CH:59]=[C:58]([O:62][CH3:63])[CH:57]=1)[C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1

Komponenten

7

Edukt 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 223948913-Carbamoyl-5-dipropylcarbamoyl-benzoic acidHCID 69869154(2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-[(3-methoxybenzyl)amino]-2-butanol Trifluoroacetate

Produkt 1

HCID 44426032N1-{(1S,2R)-1-Benzyl-2-hydroxy-3-[(3-methoxybenzyl)amino]propyl)-N3,N3-dipropyl-1,3,5-benzenetricarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
22.5 °C

Versuchsvorschrift

To a mixture of 3-(aminocarbonyl)-5-[(dipropylamino)carbonyl]benzoic acid (IX, PREPARATION 6, 0.18 g, 0.616 mmol) in dry DMF (16 mL) is added EDC (0.182 g, 0.9 mmol), HOBT (0.127 g, 0.9 mmol), triethylamine (0.062 g, 0.616 mol), and (2R,3S)-3-amino-1-[(3-methoxybenzyl)amino]-4-phenyl-2-butanol (VIII, EXAMPLE 175, 0.185 g, 0.616 mmol). The mixture is stirred at 20-25 degrees C. for 3 days. The mixture is partitioned between water and ethyl acetate. The phases are separated and the organic phase is washed three times with water. The organic phase is dried over anhydrous magnesium sulfate, filtered and concentrated. Column chromatography (silica gel, 75 mL; methanol/methylene chloride, 10/90) gives the title compound, IR (diffuse reflectance) 3306, 3301, 3270, 2962, 1676, 1667, 1663, 1645, 1638, 1627, 1615, 1550, 1537, 1450 and 1439 cm−1; NMR (CDCl3) δ 0.645, 0.968, 1.20, 1.43, 1.67, 2.8, 2.97, 3.38, 3.47, 3.73, 3.87, 4.31, 6.78, 6.91, 7.23, 7.72, 7.87, 8.22 and 8.43.

Aufarbeitung

  1. customThe mixture is partitioned between water and ethyl acetate
  2. customThe phases are separated
  3. washthe organic phase is washed three times with water
  4. dry with materialThe organic phase is dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-82f4803aa6514f62ba3dc9893e2e51d8
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727997B2

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