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tert-Butyl (R)-2-(8-(tert-butoxycarbonyloxy)-2-oxo-1,2-dihydroquinolin-5-yl)-2-(tert-butyldimethylsilyloxy)ethyl((R)-1-(3-(hydroxymethyl)phenyl)propan-2-yl)carbamate → tert-Butyl (R)-2-(8-(tert-butoxycarbonyloxy)-2-oxo-1,2-dihydroquinolin-5-yl)-2-(tert-butyldimethylsilyloxy)ethyl((R)-1-(3-formylphenyl)propan-2-yl)carbamate

HRID 471297
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 471297
[C:1]([O:5][C:6]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C@@H:20]([O:41][Si:42]([C:45]([CH3:48])([CH3:47])[CH3:46])([CH3:44])[CH3:43])[CH2:21][N:22]([C@H:30]([CH3:40])[CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([CH2:38][OH:39])[CH:33]=2)[C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)=[O:7])([CH3:4])([CH3:3])[CH3:2]>ClCCl.[O-2].[Mn+4].[O-2]>[C:1]([O:5][C:6]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C@@H:20]([O:41][Si:42]([C:45]([CH3:46])([CH3:48])[CH3:47])([CH3:44])[CH3:43])[CH2:21][N:22]([C@H:30]([CH3:40])[CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([CH:38]=[O:39])[CH:33]=2)[C:23](=[O:29])[O:24][C:25]([CH3:27])([CH3:26])[CH3:28])=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)=[O:7])([CH3:2])([CH3:3])[CH3:4]
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Komponenten

4

Edukt 1

HCID 57989031tert-Butyl (R)-2-(8-(tert-butoxycarbonyloxy)-2-oxo-1,2-dihydroquinolin-5-yl)-2-(tert-butyldimethylsilyloxy)ethyl((R)-1-(3-(hydroxymethyl)phenyl)propan-2-yl)carbamate

Produkt 1

HCID 57989227tert-Butyl (R)-2-(8-(tert-butoxycarbonyloxy)-2-oxo-1,2-dihydroquinolin-5-yl)-2-(tert-butyldimethylsilyloxy)ethyl((R)-1-(3-formylphenyl)propan-2-yl)carbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418406HCID 178418406, VerbindungKatalysator2×
HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

tert-Butyl (R)-2-(8-(tert-butoxycarbonyloxy)-2-oxo-1,2-dihydroquinolin-5-yl)-2-(tert-butyldimethylsilyloxy)ethyl((R)-1-(3-(hydroxymethyl)phenyl)propan-2-yl)carbamate (Example 276, step g) (0.609 g) was dissolved in dichloromethane (30 mL), treated with manganese (IV) oxide (0.791 g) and the resulting suspension stirred at room temperature over a weekend. More manganese (IV) oxide (0.801 g) was added and the suspension was stirred for a further 4 hours. The mixture was filtered through diatomaceous earth, washing the residue well with DCM, and the combined filtrate and washings were concentrated in vacuo to afford the subtitled compound. Yield 0.521 g. Material used immediately in the next step.

Aufarbeitung

  1. stirringthe suspension was stirred for a further 4 hours
  2. filtrationThe mixture was filtered through diatomaceous earth
  3. washwashing the residue well with DCM
  4. concentrationthe combined filtrate and washings were concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b6d6545346d444aea43d4332c3f1cf7b
Quelldatensatz
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08629271B2

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