Triphenylphosphine → HCID 54298093, compound

HRID 2228792Notes

Reaction equation

HRID 2228792 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[OH:13][C:14]1[CH:15]=[C:16]([CH2:20][C:21]#[N:22])[CH:17]=[CH:18][CH:19]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:42]([N:49]1[CH2:55][CH2:54][CH2:53][C@@H:50]1[CH2:51]O)([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43]>O1CCCC1>[C:21]([CH2:20][C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=1)[O:13][CH2:51][C@H:50]1[CH2:53][CH2:54][CH2:55][N:49]1[C:42]([O:44][C:45]([CH3:46])([CH3:48])[CH3:47])=[O:43])#[N:22]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 688279N-(tert-Butoxycarbonyl)-D-prolinolHCID 137810422-(3-Hydroxyphenyl)acetonitrile

Product 1

HCID 54298093HCID 54298093, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (3.92 g, 22.5 mmol) was added dropwise to a solution of 3-hydroxyphenyl acetonitrile (3.0 g, 22.5 mmol), triphenylphosphine (5.90 g, 22.5 mmol) and Boc-(R)-prolinol (4.53 g, 22.5 mmol) in tetrahydrofuran (30 ml), and the reaction stirred at room temperature for 18 hrs. The mixture was evaporated under reduced pressure and the residue partitioned between dichloromethane and water. The layers were separated, the organic phase washed with water, dried over MgSO4 and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel using an elution gradient of dichloromethane:pentane:methanol (80:20 to 100:0:0 to 95:0:5) to give the title compound, (2.69 g, 38%).

Workup

  1. customThe mixture was evaporated under reduced pressure
  2. customthe residue partitioned between dichloromethane and water
  3. customThe layers were separated
  4. washthe organic phase washed with water
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by column chromatography on silica gel using an elution gradient of dichloromethane:pentane:methanol (80:20 to 100:0:0 to 95:0:5)

Sources & evidence

ORD record
ord-e8c26d76779c4a17ac00006cc196cd1f
Source dataset
uspto-grants-2002_07
Patent number
US06417203B1

Reaction notes

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