Diisopropylethylamine → HCID 117995797, Verbindung

HRID 1488297Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1488297
[C@@H:1]1([O:11][CH2:12][CH2:13][NH:14][C:15](=[O:58])[CH2:16][N:17]([CH2:35][C:36]([NH:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][C:44](OC2C(F)=C(F)C(F)=C(F)C=2F)=[O:45])=[O:37])[CH2:18][C:19](=[O:34])[NH:20][CH2:21][CH2:22][O:23][C@@H:24]2[O:32][C@@H:31]([CH3:33])[C@@H:29]([OH:30])[C@@H:27]([OH:28])[C@@H:25]2[OH:26])[O:9][C@@H:8]([CH3:10])[C@@H:6]([OH:7])[C@@H:4]([OH:5])[C@@H:2]1[OH:3].Cl.[NH2:60][CH2:61][C@@H:62]([C:81]([OH:83])=[O:82])[NH:63][C:64]([O:66][CH2:67][CH:68]1[C:80]2[CH:79]=[CH:78][CH:77]=[CH:76][C:75]=2[C:74]2[C:69]1=[CH:70][CH:71]=[CH:72][CH:73]=2)=[O:65].CCN(C(C)C)C(C)C>CN(C=O)C>[O:58]=[C:15]([NH:14][CH2:13][CH2:12][O:11][C@@H:1]1[O:9][C@@H:8]([CH3:10])[C@@H:6]([OH:7])[C@@H:4]([OH:5])[C@@H:2]1[OH:3])[CH2:16][N:17]([CH2:35][C:36]([NH:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][C:44]([NH:60][CH2:61][C@@H:62]([C:81]([OH:83])=[O:82])[NH:63][C:64]([O:66][CH2:67][CH:68]1[C:69]2[CH:70]=[CH:71][CH:72]=[CH:73][C:74]=2[C:75]2[C:80]1=[CH:79][CH:78]=[CH:77][CH:76]=2)=[O:65])=[O:45])=[O:37])[CH2:18][C:19]([NH:20][CH2:21][CH2:22][O:23][C@@H:24]1[O:32][C@@H:31]([CH3:33])[C@@H:29]([OH:30])[C@@H:27]([OH:28])[C@@H:25]1[OH:26])=[O:34]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 49853440HCID 49853440, VerbindungHCID 117995923HCID 117995923, Verbindung

Produkt 1

HCID 117995797HCID 117995797, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred solution of pentafluorophenyl 6-[({bis[2-({2-[(α-L-fucopyranosyl)oxy]ethyl}amino)-2-oxoethyl]amino}acetyl)amino]hexanoate (270 mg, 0.318 mmol) in DMF at 0° C. was added 3-amino-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine hydrochloride (303 mg, 0.306 mmol) and, 5 min later, DIPEA (111 μL, 0.636 mmol). After stirring at 0° C. for 2 hr, the reaction mixture was concentrated and the residue was purified by flash chromatography on silica gel (22 g), eluting first with 100 mL of EtOAc and then 0-20% of Solvent B in Solvent A (Solvent A: v/v EtOAc/MeOH/AcCN/H2O: 6/1/1/1; Solvent B v/v EtOAc/MeOH/AcCN/H2O: 2/1/1/1) to afford the title compound. LC-MS Method A: m/e=991.66 [M+1]; Rt=1.84 min.

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated
  2. customthe residue was purified by flash chromatography on silica gel (22 g)
  3. washeluting first with 100 mL of EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-c4ee1b5c249b4f26a5dbf742f61f6ec8
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09427475B2

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