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(5-Methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-nitrophenyl carbonate → 2-[2-Chloro-1-(3,4,5-trihydroxy-6-methylsulfanyl-tetrahydro-pyran-2-yl)-propylcarbamoyl]-5-propyl-azepane-1-carboxylic acid 5-methyl-2-oxo-[1,3]dioxol-4-ylmethyl ester

HRID 901470
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 901470
[Cl:1][CH:2]([CH3:28])[CH:3]([NH:15][C:16]([CH:18]1[CH2:24][CH2:23][CH:22]([CH2:25][CH2:26][CH3:27])[CH2:21][CH2:20][NH:19]1)=[O:17])[CH:4]1[CH:9]([OH:10])[CH:8]([OH:11])[CH:7]([OH:12])[CH:6]([S:13][CH3:14])[O:5]1.[N+](C1C=CC([O:38][C:39](=O)[O:40][CH2:41][C:42]2[O:43][C:44](=[O:48])[O:45][C:46]=2[CH3:47])=CC=1)([O-])=O>CN(C=O)C>[CH3:47][C:46]1[O:45][C:44](=[O:48])[O:43][C:42]=1[CH2:41][O:40][C:39]([N:19]1[CH2:20][CH2:21][CH:22]([CH2:25][CH2:26][CH3:27])[CH2:23][CH2:24][CH:18]1[C:16](=[O:17])[NH:15][CH:3]([CH:4]1[CH:9]([OH:10])[CH:8]([OH:11])[CH:7]([OH:12])[CH:6]([S:13][CH3:14])[O:5]1)[CH:2]([Cl:1])[CH3:28])=[O:38]
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Komponenten

4

Edukt 2

HCID 10756264(5-Methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-nitrophenyl carbonateHCID 730964105-Propyl-azepane-2-carboxylic acid [2-chloro-1-(3,4,5-trihydroxy-6-methylsulfanyl-tetrahydro-pyran-2-yl)-propyl]-amide

Produkt 1

HCID 692210762-[2-Chloro-1-(3,4,5-trihydroxy-6-methylsulfanyl-tetrahydro-pyran-2-yl)-propylcarbamoyl]-5-propyl-azepane-1-carboxylic acid 5-methyl-2-oxo-[1,3]dioxol-4-ylmethyl esterAusbeute 33,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

The title compound from example 47 (54 mg, 0.12 mmol) was dissolved in dry DMF (5 mL), then solid KHCO3 (25 mg, 0.25 mmol) and carbonic acid 5-methyl-2-oxo-[1,3]dioxol-4-ylmethyl ester 4-nitro-phenyl ester (40 mg, 0.14 mmol prepared as described in F. Sakamoto, et. al, Chem. Pharm. Bull. 1984, 32 (6), 2241-2348) were added. The resulting mixture was stirred for 16 h, and the solvents were removed under reduced pressure, then the residue was purified by chromatography on silica with 5% MeOH/DCM to provide the title compound (24 mg, 33%) as a white solid.

Aufarbeitung

  1. customthe solvents were removed under reduced pressure
  2. customthe residue was purified by chromatography on silica with 5% MeOH/DCM

Quellen und Nachweise

ORD-Eintrag
ord-8e5d262ea6a94787a9c715c5512b5d39
Quelldatensatz
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07361743B2

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