1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 2-(4-(2-Bromo-6-phthalimidohexanoyl-amino)-3-oxo-1,3,4,5-tetrahydro-benzo[c]azepin-2-yl)-4-methyl-valeric acid t-butyl ester

HRID 1264550

Reaktionsgleichung

Reaktionsgleichung von HRID 1264550
[NH2:1][CH:2]1[C:8](=[O:9])[N:7]([CH:10]([CH2:18][CH:19]([CH3:21])[CH3:20])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6][C:5]2[CH:22]=[CH:23][CH:24]=[CH:25][C:4]=2[CH2:3]1.[Br:26][CH:27]([CH2:31][CH2:32][CH2:33][CH2:34][N:35]1[C:39](=[O:40])[C:38]2=[CH:41][CH:42]=[CH:43][CH:44]=[C:37]2[C:36]1=[O:45])[C:28](O)=[O:29].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1>ClCCl>[C:14]([O:13][C:11](=[O:12])[CH:10]([N:7]1[C:8](=[O:9])[CH:2]([NH:1][C:28](=[O:29])[CH:27]([Br:26])[CH2:31][CH2:32][CH2:33][CH2:34][N:35]2[C:39](=[O:40])[C:38]3=[CH:41][CH:42]=[CH:43][CH:44]=[C:37]3[C:36]2=[O:45])[CH2:3][C:4]2[CH:25]=[CH:24][CH:23]=[CH:22][C:5]=2[CH2:6]1)[CH2:18][CH:19]([CH3:21])[CH3:20])([CH3:17])([CH3:16])[CH3:15]

Komponenten

6

Edukt 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 136226402-Bromo-6-(1,3-dioxoisoindolin-2-yl)hexanoic AcidHCID 865855102-(4-Amino-3-oxo-1,3,4,5-tetrahydro-benzo[c]azepin-2-yl)-4-methyl-valeric acid, tert-butyl ester

Produkt 1

HCID 538847672-(4-(2-Bromo-6-phthalimidohexanoyl-amino)-3-oxo-1,3,4,5-tetrahydro-benzo[c]azepin-2-yl)-4-methyl-valeric acid t-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Combine 2-(4-amino-3-oxo-1,3,4,5-tetrahydro-benzo[c]azepin-2-yl)-4-methyl-valeric acid, tert-butyl ester (0.34 mmol), 2-bromo-6-phthalimidohexanoic acid (0.189 g, 0.56 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.106 g, 0.55 mmol), and 1-hydroxybenztriazole hydrate ((75 mg, 0.56 mmol) in dicloromethane (8 mL). After 17 hours, evapoarte in vacuo to give a residue, partition the residue between ethyl aceate and an aqueous 5% sulfuric acid solution (about 20 mL). Separate the layers, extract the organic layer with a saturate aqueiosu sodium bicarbonate solution and then brine, dry over Na2SO4, filter, and evaporate in vacuo to give the title compound.

Aufarbeitung

  1. customevapoarte in vacuo to give a residue
  2. custompartition the residue between ethyl aceate
  3. customSeparate the layers
  4. extractionextract the organic layer with a saturate aqueiosu sodium bicarbonate solution
  5. dry with materialbrine, dry over Na2SO4
  6. filtrationfilter
  7. customevaporate in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-62dc9a37de174468a55a0c263a849e4a
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06544980B2

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