1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Methyl-2-{2-[4-(3-o-tolyl-ureido)-phenyl]-acetylamino}-pentanoic acid benzyl ester

HRID 277194Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 277194
[C:1]1([CH3:21])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8](=[O:20])[NH:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]([OH:19])=O)=[CH:12][CH:11]=1.[CH2:22]([O:29][C:30](=[O:37])[C@H:31]([CH2:33][CH:34]([CH3:36])C)[NH2:32])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[CH:38]1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C.O.C(N(CC)CC)C>[CH2:22]([O:29][C:30](=[O:37])[C:31]([CH3:38])([NH:32][C:17](=[O:19])[CH2:16][C:13]1[CH:12]=[CH:11][C:10]([NH:9][C:8]([NH:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[CH3:21])=[O:20])=[CH:15][CH:14]=1)[CH2:33][CH2:34][CH3:36])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Komponenten

8

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 6451313Benzyl L-leucinateHCID 66052544-((((2-Methylphenyl)amino)carbonyl)amino)benzeneacetic acid

Produkt 1

HCID 69693211Methyl-2-{2-[4-(3-o-tolyl-ureido)-phenyl]-acetylamino}-pentanoic acid benzyl esterAusbeute 77,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a stirred solution of [4-(3-o-tolyl-ureido)-phenyl]-acetic acid (3.0 g), L-leucine benzyl ester (4.2 g), triethylamine (1.6 ml), and HOBT (1.6 g) in dry DMF (50 ml) at room temperature was added EDCI (2.4 g). After 16 h the mixture was poured into water (400 ml) and extracted with EtOAc (400 ml×2). The combined organics were washed with 5% citric acid (100 ml); saturated NaHCO3 (100 ml); water (100 ml), brine (100 ml); dried over MgSO4; filtered, and concentrated under reduced pressure to about 100 ml. The resulting suspension was filtered to give 4.0 g of the title compound as a white solid. MS [M+1]+488.2; 1H nmr (400 MHz, DMSO-d6) δ0.79 (d, J=6.4 Hz, 3H), 0.86 (d, J=6.4 Hz, 3H), 1.45-1.63 (m, 3H), 2.21 (s, 3H), 3.37 (s, 2H), 4.26-4.31 (m, 1H), 5.07 (s, 2H), 6.91 (t, 1H), 7.09-7.15 (m, 4H), 7.29-7.37 (m, 7H), 7.81 (d, 1H), 7.86 (s, 1H), 8.44 (d, 1H), 8.93 (s, 1H).

Aufarbeitung

  1. extractionextracted with EtOAc (400 ml×2)
  2. washThe combined organics were washed with 5% citric acid (100 ml)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure to about 100 ml
  6. filtrationThe resulting suspension was filtered

Quellen und Nachweise

ORD-Eintrag
ord-e4148f90a0584aa9b756a5ddd1486a64
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06355662B1

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