Triphenylphosphine → HCID 58009422, compound

HRID 1009480Notes

Reaction equation

HRID 1009480 reaction equation
O[CH2:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][CH:15]=1)[O:6][C@H:7]([CH3:12])[C:8]([O:10][CH3:11])=[O:9].[NH:16]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1(C)C=CC=CC=1>[C:27]([O:26][C:24]([N:16]([CH2:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][CH:15]=1)[O:6][C@H:7]([CH3:12])[C:8]([O:10][CH3:11])=[O:9])[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[O:25])([CH3:30])([CH3:29])[CH3:28]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 279800Di-tert-butyl IminodicarboxylateHCID 58009652HCID 58009652, compound

Product 1

HCID 58009422HCID 58009422, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

300 mg of methyl (2R)-2-[3-(hydroxymethyl)phenoxy]propionate, 465 mg of di-tert-butyl iminodicarboxylate, and 543 mg of triphenylphosphine were dissolved in 3.00 mL of toluene, and 445 mg of diisopropyl azodicarboxylate was added thereto under ice-cooling, followed by stirring at room temperature overnight. The reaction liquid was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5 to 0:100) to obtain 584 mg of methyl (2R)-2-(3-{[bis(tert-butoxycarbonyl)amino]methyl}phenoxy)propionate.

Workup

  1. temperatureunder ice-cooling
  2. customThe reaction liquid
  3. concentrationwas concentrated under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5 to 0:100)

Sources & evidence

ORD record
ord-c20246c024d54b3196eaedecafa49ce7
Source dataset
uspto-grants-2011_07
Patent number
US07973078B2

Reaction notes

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