Hydrochloric Acid → 1-Acetyl-3-(2-methoxycarbonylamino-3-methyl-butyryl)-imidazolidine-4-carboxylic acid methyl ester

HRID 417509Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 417509
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][N:8]([C:10](OC(C)(C)C)=[O:11])[CH2:7][N:6]1[C:17](=[O:27])[CH:18]([NH:22][C:23]([O:25][CH3:26])=[O:24])[CH:19]([CH3:21])[CH3:20])=[O:4].Cl.[CH:29](N(C(C)C)CC)(C)C.C(OC(=O)C)(=O)C>ClCCl>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][N:8]([C:10](=[O:11])[CH3:29])[CH2:7][N:6]1[C:17](=[O:27])[CH:18]([NH:22][C:23]([O:25][CH3:26])=[O:24])[CH:19]([CH3:21])[CH3:20])=[O:4]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 666211143-(2-Methoxycarbonylamino-3-methyl-butyryl)-imidazolidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-methyl ester

Produkt 1

HCID 666209721-Acetyl-3-(2-methoxycarbonylamino-3-methyl-butyryl)-imidazolidine-4-carboxylic acid methyl esterAusbeute 69,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

3-(2-Methoxycarbonylamino-3-methyl-butyryl)-imidazolidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-methyl ester (465 mg, 1.2 mmol) was dissolved in dichloromethane (1 mL) and HCl (4M dioxane, 3 mL) was added. The resultant suspension was stirred at room temperature for 30 minutes, after which all volatiles were removed in vacuo. The crude material was dissolved in THF and diisopropyl ethylamine (154 mg, 1.2 mmol) was added, followed by acetic anhydride (122 mg, 1.2 mmol). The reaction was stirred at room temperature. After 30 minutes, all volatiles were removed in vacuo. The crude material was purified by silica gel chromatography (eluent: DCM/MeOH) to yield the product 1-Acetyl-3-(2-methoxycarbonylamino-3-methyl-butyryl)-imidazolidine-4-carboxylic acid methyl ester (273 mg, 0.829 mmol): LCMS-ESI+: calc'd for C14H23N3O6: 329.4 (M+). Found: 330.4 (M+H+).

Aufarbeitung

  1. customafter which all volatiles were removed in vacuo
  2. dissolutionThe crude material was dissolved in THF
  3. customall volatiles were removed in vacuo
  4. customThe crude material was purified by silica gel chromatography (eluent: DCM/MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-8b6367d647d74c9ea47e9111e3d154c8
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088368B2

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