Triphenylphosphine → HCID 137328571, compound
Reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([OH:8])[CH:7]=1.[C:9]([O:13][C:14](=[O:28])[NH:15][C@@H:16]([C:19]([CH3:27])([CH3:26])[O:20][SiH2:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:17]O)([CH3:12])([CH3:11])[CH3:10].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>>[C:9]([O:13][C:14](=[O:28])[NH:15][C@@H:16]([C:19]([CH3:27])([CH3:26])[O:20][SiH2:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:17][O:8][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([Br:1])[CH:7]=1)([CH3:12])([CH3:10])[CH3:11]Participants
5
Conditions
- Temperature
- 0 °C
Procedure
A 100 mL RBF was charged with 3-bromo-5-hydroxypyridine (1.20 g, 6.87 mmol), (R)-[1-(tert-butyl-dimethyl-silanyloxymethyl)-2-hydroxy-ethyl]-carbamic acid tert-butyl ester (2.1 g, 6.87 mmol) and Ph3P (2.34 g, 8.93 mmol), and was purged with nitrogen. THF (30 mL) was added at 0° C. After stirring at 0° C. for 10 min, DEAD (1.41 mL, 8.93 mmol) was added via syringe. The reaction mixture was stirred at 0° C. for 0.5 h and at rt for 2 h. The reaction mixture was concentrated and the residue was separated by flash chromatography (5-25% EtOAc in hexane) to provide the desired product (3.14 g, 99%). MS (DCI) m/z 461, 463 (M+1)+.
Workup
- customwas purged with nitrogen
- additionTHF (30 mL) was added at 0° C
- stirringThe reaction mixture was stirred at 0° C. for 0.5 h and at rt for 2 h
- concentrationThe reaction mixture was concentrated
- customthe residue was separated by flash chromatography (5-25% EtOAc in hexane)
Sources & evidence
- ORD record
- ord-2302640e31134c1b9ec7b12673d85b0b
- Source dataset
- uspto-grants-2004_12
- Patent number
- US06831175B2
Reaction notes
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