(r)-Tert-butyl 5-(1-(tert-butyldimethylsilyloxy)-2-(1-(3-(hydroxymethyl)phenyl)-2-methylpropan-2-ylamino)ethyl)-2-oxo-1,2-dihydroquinolin-8-yl carbonate → (r)-Tert-butyl 5-(1-(tert-butyldimethylsilyloxy)-2-(1-(3-formylphenyl)-2-methylpropan-2-ylamino)ethyl)-2-oxo-1,2-dihydroquinolin-8-yl carbonate

HRID 1689518Notes

Reaction equation

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

Participants

Conditions

Temperature: 20 °C

Procedure

Manganese dioxide (0.6 g) was added to a solution of (R)-tert-butyl 5-(1-(tert-butyldimethylsilyloxy)-2-(1-(3-(hydroxymethyl)phenyl)-2-methylpropan-2-ylamino)ethyl)-2-oxo-1,2-dihydroquinolin-8-yl carbonate (Example 275, step f) (0.44 g) in dichloromethane (30 mL) and the mixture stirred vigorously at 20° C. for 3 hours. The reaction mixture was filtered through diatomaceous earth and the solvent removed under reduced pressure to afford the subtitled compound. Yield 0.42 g.

Workup

filtrationThe reaction mixture was filtered through diatomaceous earth
customthe solvent removed under reduced pressure

Sources & evidence

ORD record: ord-349f825ac382475e9e5fc02d9f6b93f3
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148373B2

Reaction notes

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