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Hydrochloric Acid → N-[(3R*,4R*)-1-Benzyl-4-(isopropylamino-methyl)-pyrrolidin-3-ylmethyl]-N-isopropyl-4-methoxy-3-(3-methoxy-propoxy)-benzamide

HRID 1158485
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1158485
C(OC(=O)[N:7]([CH2:11][C@H:12]1[C@@H:16]([CH2:17][N:18]([CH:35]([CH3:37])[CH3:36])[C:19](=[O:34])[C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH2:29][CH2:30][CH2:31][O:32][CH3:33])[CH:21]=2)[CH2:15][N:14]([CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH2:13]1)[CH:8]([CH3:10])[CH3:9])(C)(C)C.Cl>O1CCOCC1>[CH2:38]([N:14]1[CH2:13][C@@H:12]([CH2:11][NH:7][CH:8]([CH3:10])[CH3:9])[C@@H:16]([CH2:17][N:18]([CH:35]([CH3:37])[CH3:36])[C:19](=[O:34])[C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH2:29][CH2:30][CH2:31][O:32][CH3:33])[CH:21]=2)[CH2:15]1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1
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Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 59512411[(3S*,4R*)-1-Benzyl-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidin-3-ylmethyl]-isopropyl-carbamic acid tert-butyl ester

Produkt 1

HCID 59512319N-[(3R*,4R*)-1-Benzyl-4-(isopropylamino-methyl)-pyrrolidin-3-ylmethyl]-N-isopropyl-4-methoxy-3-(3-methoxy-propoxy)-benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-Dioxane
Lösungsmittel

Versuchsvorschrift

To a solution of [(3S*,4R*)-1-benzyl-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidin-3-ylmethyl]-isopropyl-carbamic acid tert-butyl ester (0.41 g, 0.66 mmol), is added a dioxane solution of HCl 4N (10 mL). The reaction mixture is stirred for 2 h at room temperature. The solvent is concentrated and water (20 mL), an aqueous solution of NaOH 4N (5 mL) and Et2O (25 mL) are added. The layers are separated and the aqueous one extracted twice with Et2O. The combined organic extracts are dried (MgSO4), and the solvent is removed in vacuo to give the title compound which is used without further purification in the next step. MS (LC-MS): 526.4 [M+H]+; tR (HPLC, C18 column, 10-100% CH3CN/H2O/5 min, 100% CH3CN/2.53 min, CH3CN and H2O containing 0.1% TFA, flow: 1.5 mL/min): 4.78 min.

Aufarbeitung

  1. concentrationThe solvent is concentrated
  2. additionwater (20 mL), an aqueous solution of NaOH 4N (5 mL) and Et2O (25 mL) are added
  3. customThe layers are separated
  4. extractionthe aqueous one extracted twice with Et2O
  5. dry with materialThe combined organic extracts are dried (MgSO4)
  6. customthe solvent is removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-fb7d4b704157403aa6335ec8f7a56afc
Quelldatensatz
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07807709B2

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