Triphenylphosphine → HCID 66653360, compound

HRID 1524273Notes

Reaction equation

HRID 1524273 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.[CH2:12]([O:19][C:20](=[O:24])[C@@H:21](O)[CH3:22])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.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:21]([C:20]([O:19][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:24])[CH3:22])[CH:5]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 88068Methyl 3-HydroxybenzoateHCID 5462977Diethyl azodicarboxylateHCID 11052238benzyl (2S)-2-hydroxypropanoate

Product 1

HCID 66653360HCID 66653360, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (10.0 g, 55.5 mmol) of 3-hydroxy-benzoic acid methyl ester in tetrahydrofuran (125 mL), cooled to 0° C., is added (8.44 g, 55.5 mmol) of (S)-2-hydroxy-propionic acid benzyl ester, and (14.5 g, 55.5 mmol) of triphenyl phosphine. To this mixture is added a solution of (11.3 mL, 72.2 mmol) of diethylazodicarboxylate in tetrahydrofuran (25 mL) via a syringe pump over a 1 hour period. The reaction mixture is warmed to room temperature and stirred for 18 h then concentrated under reduced pressure. The residue is purified by flash silica gel chromatography to provide 13 g of 3-((R)-1-benzyloxycarbonyl-ethoxy)-benzoic acid methyl ester as an oil.

Workup

  1. concentrationthen concentrated under reduced pressure
  2. customThe residue is purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-808cd97d3b094f2aa7ada8ed006cd444
Source dataset
uspto-grants-2015_07
Patent number
US09079880B2

Reaction notes

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