StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Diisopropylethylamine → (S)-methyl 5-(4-iodobenzylamino)-4-((S)-5-methoxy-5-oxo-2-(3-(4-sulfamoylphenyl)thioureido)pentanamido)-5-oxopentanoate

HRID 333133
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 333133
[NH2:1][C@H:2]([C:9]([NH:11][C@@H:12]([CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])[C:13]([NH:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([I:23])=[CH:19][CH:18]=1)=[O:14])=[O:10])[CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6].[N:30]([C:33]1[CH:38]=[CH:37][C:36]([S:39]([NH2:42])(=[O:41])=[O:40])=[CH:35][CH:34]=1)=[C:31]=[S:32].CCN(C(C)C)C(C)C>C(#N)C>[I:23][C:20]1[CH:19]=[CH:18][C:17]([CH2:16][NH:15][C:13](=[O:14])[C@@H:12]([NH:11][C:9](=[O:10])[C@@H:2]([NH:1][C:31]([NH:30][C:33]2[CH:34]=[CH:35][C:36]([S:39](=[O:41])(=[O:40])[NH2:42])=[CH:37][CH:38]=2)=[S:32])[CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6])[CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])=[CH:22][CH:21]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 5213594-IsothiocyanatobenzenesulfonamideHCID 68632742(S)-methyl 4-amino-5-((S)-1-(4-iodobenzylamino)-5-methoxy-1,5-dioxopentan-2-ylamino)-5-oxopentanoate

Produkt 1

HCID 86632285(S)-methyl 5-(4-iodobenzylamino)-4-((S)-5-methoxy-5-oxo-2-(3-(4-sulfamoylphenyl)thioureido)pentanamido)-5-oxopentanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342
Acetonitrile
Lösungsmittel

Versuchsvorschrift

A solution of (S)-methyl 4-(tert-butoxycarbonylamino)-5-((S)-1-(4-iodobenzylamino)-5-methoxy-1,5-dioxopentan-2-ylamino)-5-oxopentanoate (0.448 g, 0.723 mmol) in DCM (10 mL) and TFA (4.0 mL) was stirred at room temperature overnight. After the solvent was evaporated, the reaction mixture was diluted with DCM, washed with sat. K2CO3 and concentrated in vacuo to afford (S)-methyl 4-amino-5-((S)-1-(4-iodobenzylamino)-5-methoxy-1,5-dioxopentan-2-ylamino)-5-oxopentanoate. A solution of the above product ((S)-methyl 4-amino-5-((S)-1-(4-iodobenzylamino)-5-methoxy-1,5-dioxopentan-2-ylamino)-5-oxopentanoate), 4-isothiocyanatobenzenesulfonamide (0.171 g, 0.80 mmol) in acetonitrile (10 mL) containing DIPEA (0.40 mL) was stirred at room temperature under nitrogen for 48 h. The solvent was evaporated under reduced pressure to give a crude product, which was purified by flash chromatography 5% MeOH in DCM as eluent to give (S)-methyl 5-(4-iodobenzylamino)-4-((S)-5-methoxy-5-oxo-2-(3-(4-sulfamoylphenyl)thioureido)pentanamido)-5-oxopentanoate (0.469 g) as a white solid. MS (ESI), 756 (M+Na)+, 377 (M/2+H)+.

Aufarbeitung

  1. customThe solvent was evaporated under reduced pressure
  2. customto give a crude product, which
  3. customwas purified by flash chromatography 5% MeOH in DCM as eluent

Quellen und Nachweise

ORD-Eintrag
ord-ff1e856f9c3c4098ae9902dea324907f
Quelldatensatz
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08877970B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion