Triphenylphosphine → HCID 86666327, compound

HRID 1026357Notes

Reaction equation

HRID 1026357 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[CH3:15][O:16][CH2:17][O:18][C:19]1[CH:35]=[CH:34][C:22]2[CH2:23][C:24]([C:27]3[N:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=3)([CH3:26])[O:25][C:21]=2[CH:20]=1.O[CH2:37][C@@H:38]([NH:40][C:41](=[O:47])[O:42][C:43]([CH3:46])([CH3:45])[CH3:44])[CH3:39].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[CH3:15][O:16][CH2:17][O:18][C:19]1[CH:35]=[CH:34][C:22]2[CH2:23][C:24]([C:27]3[N:32]=[CH:31][C:30]([O:33][CH2:39][C@@H:38]([NH:40][C:41](=[O:47])[O:42][C:43]([CH3:44])([CH3:46])[CH3:45])[CH3:37])=[CH:29][CH:28]=3)([CH3:26])[O:25][C:21]=2[CH:20]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 70231031,1-Dimethylethyl N-((1S)-2-hydroxy-1-methylethyl)carbamateHCID 67777325HCID 67777325, compound

Product 1

HCID 86666327HCID 86666327, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of diisopropyl azodicarboxylate (1.9 M in toluene, 2.20 mL) was added dropwise to a solution of diastereomer of 6-(6-(methoxymethoxy)-2-methyl-2,3-dihydrobenzofuran-2-yl)pyridin-3-ol (shorter retention time, 800 mg), (S)-tert-butyl (1-hydroxypropan-2-yl)carbamate (976 mg), and triphenylphosphine (1100 mg) in toluene (20 mL) at ambient temperature. The mixture was stirred at room temperature for 2 hr. The mixture was concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water. The separated organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (hexane/ethyl acetate) to give the title compound (1100 mg).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and water
  3. washThe separated organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-890be229caca43809e2c61393fe41f5c
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

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