Triphenylphosphine → HCID 89590639, compound

HRID 522411Notes

Reaction equation

HRID 522411 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[C@H:10]1[C:37](=[O:38])[N:36]2[CH2:39][C@@H:33]([CH2:34][C@H:35]2[C:40]([O:42][CH3:43])=[O:41])[O:32][C:22]2=[N:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:29]=3[C:30]([OH:31])=[C:21]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][C@@H:15]2[CH2:44][C@H:14]2[O:13][C:12](=[O:45])[NH:11]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:65][N:66]([CH3:71])[CH2:67][CH2:68][CH2:69]O.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[C@H:10]1[C:37](=[O:38])[N:36]2[CH2:39][C@@H:33]([CH2:34][C@H:35]2[C:40]([O:42][CH3:43])=[O:41])[O:32][C:22]2=[N:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:29]=3[C:30]([O:31][CH2:69][CH2:68][CH2:67][N:66]([CH3:71])[CH3:65])=[C:21]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][C@@H:15]2[CH2:44][C@H:14]2[O:13][C:12](=[O:45])[NH:11]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 766463-(Dimethylamino)-1-propanolHCID 178501303HCID 178501303, compound

Product 1

HCID 89590639HCID 89590639, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

A reaction tube was charged with the product of step 5 (200 mg, 0.326 mmol) and triphenylphosphine (855 mg, 3.26 mmol). The tube was sealed and THF (3259 μl) was added via syringe at 0° C. 3-dimethylamino-1-propanol (381 μl, 3.26 mmol) was added followed by slow addition of diisopropyl azodicarboxylate (631 μl, 3.26 mmol). After 5 minutes the cooling bath was removed and the mixture was allowed to reach room temperature and stirred for 10 minutes. The reaction tube was heated at 40° C. for 3 hours. The reaction mixture was concentrated to dryness in rotavap and the residue was purified on a gold cap silica gel (80 g) column (gradient: 0 to 60% solvent B in dichloromethane (solvent B: 20% methanol in ethyl acetate)) to give the title compound (210 mg, 0.300 mmol, 92% yield) as a white powder.

Workup

  1. customThe tube was sealed
  2. customAfter 5 minutes the cooling bath was removed
  3. customto reach room temperature
  4. concentrationThe reaction mixture was concentrated to dryness in rotavap
  5. customthe residue was purified on a gold
  6. customcap silica gel (80 g) column (gradient: 0 to 60% solvent B in dichloromethane (solvent B: 20% methanol in ethyl acetate))

Sources & evidence

ORD record
ord-9197bf62ecf4459390d1e6ff4831e64c
Source dataset
uspto-grants-2016_05
Patent number
US09328138B2

Reaction notes

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