Triphenylphosphine → HCID 66653468, compound

HRID 1524277Notes

Reaction equation

HRID 1524277 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([OH:10])[CH:5]=1.[C:12]([O:16][C:17](=[O:21])[C@H:18](O)[CH3:19])([CH3:15])([CH3:14])[CH3:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][C@H:18]([C:17]([O:16][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:21])[CH3:19])[CH:5]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 88068Methyl 3-HydroxybenzoateHCID 5462977Diethyl azodicarboxylateHCID 10953655tert-butyl (2R)-2-hydroxypropanoate

Product 1

HCID 66653468HCID 66653468, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Cool a solution of 3-hydroxy-benzoic acid methyl ester (0.50 g, 3.42 mmol) in tetrahydrofuran (8 mL) to 0° C., and add (R)-2-hydroxy-propionic acid tert-butyl ester (0.52 g, 3.42 mmol) and triphenyl phosphine (0.90 g, 3.42 mmol). Add diethylazodicarboxylate (0.70 mL, 4.4 mmol) to this mixture via a syringe pump over a 1 hour period. Concentrate the reaction mixture under reduced pressure and purify the residue by flash silica gel chromatography to provide 0.80 g of 3-((S)-1-tert-butoxycarbonyl-ethoxy)-benzoic acid methyl ester as an oil.

Workup

  1. concentrationConcentrate the reaction mixture under reduced pressure
  2. custompurify the residue by flash silica gel chromatography

Sources & evidence

ORD record
ord-ad242636ddb34c2f972bf2277721d193
Source dataset
uspto-grants-2015_07
Patent number
US09079880B2

Reaction notes

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