Triphenylphosphine → HCID 24862304, compound

HRID 2236121Notes

Reaction equation

HRID 2236121 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([OH:30])[CH:25]=1)[CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1.O[C@H:32]1[CH2:37][CH2:36][O:35][C:33]1=[O:34].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>C1(C)C=CC=CC=1.O>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:23][C:24]1[CH:25]=[C:26]([O:30][C@@H:32]2[CH2:37][CH2:36][O:35][C:33]2=[O:34])[CH:27]=[CH:28][CH:29]=1)[CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 11776Triphenylphosphine2×HCID 97268Di-tert-butyl azodicarboxylate2×HCID 3578532-Hydroxy-gamma-butyrolactone, (2S)-HCID 219497323-((Benzo[d]oxazol-2-yl(3-(4-methoxyphenoxy)propyl)amino)methyl)phenol

Product 1

HCID 24862304HCID 24862304, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
40 °C

Procedure

In an argon atmosphere, N-(benzoxazole-2-yl)-N-(3-(4-methoxyphenoxy)propyl)-3-hydroxybenzylamine (2.0 g), (S)-2-hydroxybutyrolactone (1.0 g), and triphenylphosphine (2.6 g) were dissolved in toluene (30 mL), and a solution of di-tert-butyl azodicarboxylate (2.3 g) in toluene (10 mL) was dropwise to the solution at 0° C., followed by stirring for 24 hours at 40° C. Subsequently, triphenylphosphine (1.3 g) and di-tert-butyl azodicarboxylate (1.1 g) were added to the mixture at 40° C., followed by stirring for 24 hours at the same temperature. The reaction mixture was returned to room temperature. Water was added thereto, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine. The washed mixture was dried over sodium sulfate anhydrate. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified through silica gel column chromatography (n-hexane/ethyl acetate=1/1), to thereby yield a colorless oil (2.2 g, 92%, 98% ee).

Workup

  1. customwas dropwise to the solution at 0° C.
  2. stirringby stirring for 24 hours at the same temperature
  3. customwas returned to room temperature
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialThe washed mixture was dried over sodium sulfate anhydrate
  7. filtrationThe reaction mixture was filtered
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe residue was purified through silica gel column chromatography (n-hexane/ethyl acetate=1/1)
  10. customto thereby yield a colorless oil (2.2 g, 92%, 98% ee)

Sources & evidence

ORD record
ord-9c7575c8a1bd4b55b66b3c78c0f05021
Source dataset
uspto-grants-2010_05
Patent number
US07714141B2

Reaction notes

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