Phthalimide → HCID 21949925, compound

HRID 2114661Notes

Reaction equation

HRID 2114661 reaction equation
[CH2:1]([C:3]1[C:7]([O:8][C:9]2[CH:10]=[C:11]([CH:14]=[C:15]([O:17][CH3:18])[CH:16]=2)[C:12]#[N:13])=[C:6]([CH2:19][CH3:20])[N:5]([CH2:21][CH2:22]O)[N:4]=1)[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(=O)[NH:47]C(=O)C2=CC=CC=C12.CC(OC(/N=N/C(OC(C)C)=O)=O)C.O.NN>O1CCCC1>[NH3:4].[NH2:47][CH2:22][CH2:21][N:5]1[C:6]([CH2:19][CH3:20])=[C:7]([O:8][C:9]2[CH:10]=[C:11]([CH:14]=[C:15]([O:17][CH3:18])[CH:16]=2)[C:12]#[N:13])[C:3]([CH2:1][CH3:2])=[N:4]1

Participants

8

Reactant 5

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 24654Hydrazine hydrate (1:1)HCID 5363146Diisopropyl azodicarboxylateHCID 21949870HCID 21949870, compound

Product 2

HCID 222AmmoniaHCID 21949925HCID 21949925, compoundYield 152.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The alcohol from Example 202 (87 mg, 0.28 mmol), triphenylphosphine (220 mg, 0.84 mmol) and phthalimide (124 mg, 0.84 mmol) were dissolved in tetrahydrofuran (5 ml) at 0° C. under nitrogen and diisopropylazodicarboxylate (165 μl, 0.84 mmol) dissolved in tetrahydrofuran (1 ml) was added dropwise. The reaction was allowed to warm to room temperature and was stirred for 18 hours. The solvent was removed under reduced pressure, the residue was dissolved in ethanol (6 ml) and hydrazine hydrate (68 μl, 1.40 mmol) was added. The slurry was stirred for 48 hours at room temperature under nitrogen, concentrated under reduced pressure and the residue was dissolved in methanol. The solution was then passed through an SCX column eluting with methanol to remove impurities, then 2M ammonia in methanol solution to elute the product. The product was then purified by flash chromatography on silica gel eluting with dichloromethane:methanol (95:5) then dichloromethane:methanol:0.88 ammonia (90:10:1, by volume) to provide the title compound (67 mg) as an oil.

Workup

  1. additionwas added dropwise
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in ethanol (6 ml)
  4. stirringThe slurry was stirred for 48 hours at room temperature under nitrogen
  5. concentrationconcentrated under reduced pressure
  6. dissolutionthe residue was dissolved in methanol
  7. washeluting with methanol
  8. customto remove impurities
  9. wash2M ammonia in methanol solution to elute the product
  10. customThe product was then purified by flash chromatography on silica gel eluting with dichloromethane:methanol (95:5)

Sources & evidence

ORD record
ord-90c3de576f224637b57dae2eba310610
Source dataset
uspto-grants-2008_10
Patent number
US07435728B2

Reaction notes

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