Diisopropylethylamine → Methyl 2-[(5-{[2-(acetylamino)-3-(4-{2-[(benzhydryloxy)carbonyl][(benzyloxy)(oxo)acetyl]anilino}-3-ethylphenyl)propanoyl]amino}pentyl)oxy]-6-hydroxybenzoate

HRID 488662Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 488662
N[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:16]=[CH:15][CH:14]=[C:13]([OH:17])[C:8]=1[C:9]([O:11][CH3:12])=[O:10].[C:18]([NH:21][C@H:22]([C:67]([OH:69])=O)[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]([C:53](=[O:64])[C:54]([O:56][CH2:57][C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=2)=[O:55])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[C:37]([O:39][CH:40]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[O:38])=[C:26]([CH2:65][CH3:66])[CH:25]=1)(=[O:20])[CH3:19].F[B-](F)(F)F.[N:75]1(OC(N(C)C)=[N+](C)C)[C:79]2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>CN(C)C=O.C(OCC)(=O)C>[C:18]([NH:21][CH:22]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]([C:53](=[O:64])[C:54]([O:56][CH2:57][C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=2)=[O:55])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[C:37]([O:39][CH:40]([C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)=[O:38])=[C:26]([CH2:65][CH3:66])[CH:25]=1)[C:67]([NH:75][CH2:79][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:16]=[CH:15][CH:14]=[C:13]([OH:17])[C:8]=1[C:9]([O:11][CH3:12])=[O:10])=[O:69])(=[O:20])[CH3:19]

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 11832643Methyl 2-(4-aminobutoxy)-6-hydroxybenzoateHCID 69803959N-acetyl-4-{2-[(benzhydryloxy)carbonyl][(benzyloxy)(oxo)acetyl]anilino}-3-ethylphenylalanine

Produkt 1

HCID 22271917Methyl 2-[(5-{[2-(acetylamino)-3-(4-{2-[(benzhydryloxy)carbonyl][(benzyloxy)(oxo)acetyl]anilino}-3-ethylphenyl)propanoyl]amino}pentyl)oxy]-6-hydroxybenzoateAusbeute 57,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Methyl 2-(4-aminobutoxy)-6-hydroxybenzoate (42 mg, 0.12 mmol), N-acetyl-4-{2-[(benzhydryloxy)carbonyl][(benzyloxy)(oxo)acetyl]anilino}-3-ethylphenylalanine (70 mg, 0.1 mmol), 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (32 mg, 0.1 mmol) and diisopropylethylamine (70 μL, 0.4 mmol) in N,N-dimethylformamide (1 mL) was stirred at ambient temperature overnight, diluted with ethyl acetate and washed with aqueous NaHCO3 (1×30 mL), brine (2×30 mL), dried (MgSO4), filtered and concentrate under reduced pressure. The residue was purified on silica gel eluting with ethyl acetate to provide of titled compound 54 mg.

Aufarbeitung

  1. washwashed with aqueous NaHCO3 (1×30 mL), brine (2×30 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrate under reduced pressure
  5. customThe residue was purified on silica gel eluting with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-9b6992a029ca4c3eadb4348f818fcc09
Quelldatensatz
uspto-grants-2005_12
Patentnummer
US06972340B2

Notizen zur Reaktion

Wird geladen…