Triphenylphosphine → HCID 59103876, compound

HRID 1422868Notes

Reaction equation

HRID 1422868 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:3]=1[C:4]([O-:6])=[O:5].O[CH2:13][CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19].[C:23]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1.C(OCC)(=O)C.O>[C:18]([O:17][C:16]([NH:15][CH2:14][CH2:13][O:11][C:9]1[CH:8]=[CH:7][C:3]([C:4]([O:6][CH3:23])=[O:5])=[C:2]([OH:1])[CH:10]=1)=[O:22])([CH3:21])([CH3:20])[CH3:19]

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 2733206tert-butyl N-(2-hydroxyethyl)carbamateHCID 178524491HCID 178524491, compound

Product 1

HCID 59103876HCID 59103876, compoundYield 56.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Commercially available starting materials 2,4-dihydroxybenzoate (1.04 g, 6.21 mmol), tert-butyl 2-hydroxyethylcarbamate (1.10 g, 6.82 mmol) and triphenylphosphine (1.8 g, 6.86 mmol) were dissolved in anhydrous THF (50 mL). To this solution was added diisopropyl azodicarboxylate (1.3 mL, 6.82 mmol) and the reaction was stirred for 18 h at room temperature. Water (200 mL) and ethyl acetate (200 mL) were added; the organic layer was separated, washed with water (2×200 mL), dried over MgSO4, filtered and evaporated to dryness. The crude product was purified by silcagel column chromatography eluting with a gradient from 10%-50% ethyl acetate in hexane. Fractions containing the pure desired product were combined and solvent was removed under reduced pressure to produce a white solid (1.09 g, 56%).

Workup

  1. customthe organic layer was separated
  2. washwashed with water (2×200 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe crude product was purified by silcagel column chromatography
  7. washeluting with a gradient from 10%-50% ethyl acetate in hexane
  8. additionFractions containing the pure desired product
  9. customsolvent was removed under reduced pressure

Sources & evidence

ORD record
ord-764329db3c3f4215a4df297b7f0cfc99
Source dataset
uspto-grants-2015_01
Patent number
US08927548B2

Reaction notes

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