4-Nitrophenol → HCID 86585802, compound
Reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[C:34]([O:38][C:39](=[O:61])[N:40]([CH2:44][CH:45]([O:53][Si:54]([C:57]([CH3:60])([CH3:59])[CH3:58])([CH3:56])[CH3:55])[C:46]1[CH:47]=[N:48][C:49]([Cl:52])=[CH:50][CH:51]=1)[CH2:41][CH2:42][OH:43])([CH3:37])([CH3:36])[CH3:35].[N+:62]([C:65]1[CH:70]=[CH:69][C:68](O)=[CH:67][CH:66]=1)([O-:64])=[O:63]>C1COCC1>[C:34]([O:38][C:39](=[O:61])[N:40]([CH2:44][CH:45]([O:53][Si:54]([C:57]([CH3:60])([CH3:59])[CH3:58])([CH3:55])[CH3:56])[C:46]1[CH:47]=[N:48][C:49]([Cl:52])=[CH:50][CH:51]=1)[CH2:41][CH2:42][O:43][C:68]1[CH:69]=[CH:70][C:65]([N+:62]([O-:64])=[O:63])=[CH:66][CH:67]=1)([CH3:37])([CH3:35])[CH3:36]Participants
Conditions
- Temperature
- 0 °C
Procedure
To a cooled (0° C.), stirred solution of triphenylphosphine (629 mg) in THF (6 mL) was added diisopropylazodicarboxylate (0.5 mL) dropwise and the resulting thick white slurry was stirred for 45 min. A solution of [2-(tert-butyl-dimethyl-silanyloxy)-2-(6-chloro-pyridin-3-yl)-ethyl]-(2-hydroxy-ethyl)-carbamic acid tert-butyl ester (515 mg) and 4-nitrophenol (332 mg) in THF (5 mL) was added dropwise to produce a yellow slurry. After an additional 1 h period, the cooling bath was removed and the mixture was allowed to stir at ambient temperature for 20 h. This mixture was concentrated in vacuo and chromatographed on a Biotage® F40M column (gradient of 10% to 15% ethyl acetate/hexanes) to afford 530 mg of the title compound (I-3c) as a colorless foam.
Workup
- customto produce a yellow slurry
- waitAfter an additional 1 h period
- customthe cooling bath was removed
- stirringto stir at ambient temperature for 20 h
- concentrationThis mixture was concentrated in vacuo
- customchromatographed on a Biotage® F40M column (gradient of 10% to 15% ethyl acetate/hexanes)
Sources & evidence
- ORD record
- ord-7e42f6291dda40bfb46338a76ff860d2
- Source dataset
- uspto-grants-2005_09
- Patent number
- US06939867B2
Reaction notes
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