Triphenylphosphine → (2S)-3-[4-(3-Bromopropoxy)-phenyl]-2-methoxy-propionic acid ethyl ester
Reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:20]([O:22][C:23](=[O:35])[C@@H:24]([O:33][CH3:34])[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=1)[CH3:21].[Br:36][CH2:37][CH2:38][CH2:39]O>C1(C)C=CC=CC=1.C1COCC1>[CH2:20]([O:22][C:23](=[O:35])[C@@H:24]([O:33][CH3:34])[CH2:25][C:26]1[CH:27]=[CH:28][C:29]([O:32][CH2:39][CH2:38][CH2:37][Br:36])=[CH:30][CH:31]=1)[CH3:21]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of triphenylphosphine (4.77 mmol, 1250 mg) in 50 mL of dry toluene was treated at 0° C. with diisopropilazodicarboxylate (4.77 mmol, 964.5 mg) and stirred for about 20 minutes. A solution of (2S)-3-(4-hydroxy-phenyl)-2-methoxy-propionic acid ethyl ester (Example 283, Step 1) (4.46 mmol, 1000 mg) and 3-bromo-propan-1-ol (4.77 mmol, 663 mg) in 10 mL of dry THF was added, and the mixture was stirred at room temperature overnight. The mixture was concentrated to dryness under vacuum and purified by silica gel chromatography (silica gel, hexanes/ethyl acetate 6:1). The fraction with Rf 0.4 corresponding to the coupled compound was combined and concentrated to dryness to afford a yellow oil. MS (ES) for C15H21BrO4 [M+Na]+: 367.2.
Workup
- stirringthe mixture was stirred at room temperature overnight
- concentrationThe mixture was concentrated to dryness under vacuum
- custompurified by silica gel chromatography (silica gel, hexanes/ethyl acetate 6:1)
- concentrationconcentrated to dryness
- customto afford a yellow oil
Sources & evidence
- ORD record
- ord-fd6cb9ae9ed44dd8b5b69ced36351a62
- Source dataset
- uspto-grants-2007_03
- Patent number
- US07192982B2
Reaction notes
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