Phthalimide → HCID 67976175, compound

HRID 508621Notes

Reaction equation

HRID 508621 reaction equation
O[CH2:2][CH2:3][CH2:4][C:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[N:7]([C:17]2[CH:22]=[CH:21][C:20]([S:23]([NH2:26])(=[O:25])=[O:24])=[CH:19][CH:18]=2)[N:6]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C:46]1(=[O:56])[NH:50][C:49](=[O:51])[C:48]2=[CH:52][CH:53]=[CH:54][CH:55]=[C:47]12.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[O:51]=[C:49]1[C:48]2[C:47](=[CH:55][CH:54]=[CH:53][CH:52]=2)[C:46](=[O:56])[N:50]1[CH2:2][CH2:3][CH2:4][C:5]1[CH:9]=[C:8]([C:10]2[CH:11]=[CH:12][C:13]([CH3:16])=[CH:14][CH:15]=2)[N:7]([C:17]2[CH:22]=[CH:21][C:20]([S:23]([NH2:26])(=[O:25])=[O:24])=[CH:19][CH:18]=2)[N:6]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 67974807HCID 67974807, compound

Product 1

HCID 67976175HCID 67976175, compoundYield 392.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of alcohol 18c (0.1 g, 0.27 mmol), PPh3 (0.11 g, 0.40 mmol), and phthalimide (60 mg, 0.40 mmol) in 5 mL of THF was added dropwise DIAD (54 mg, 0.27 mmol) at room temperature. The reaction mixture was stirred overnight. The solvent was evaporated, and the resulting solid was recrystallized from methanol to afford 0.53 g (87%) of the title compound as a white solid. 1H NMR (300 MHz, CDCl3): δ 7.84-7.76 (m, 1H), 7.70-7.65 (m, 1H), 7.34 (d, J=8.76 Hz, 1H), 7.11 (d, J=7.89 Hz, 1H), 7.00 (d, J=8.15 Hz, 1H), 6.33 (s, 1H), 4.96 (s, 1H), 3.85 (t, J=6.96, 6.96 Hz, 1H), 2.80 (t, J=7.47, 7.47 Hz, 1H), 2.35 (s, 1H), 2.24-2.13 (m, 1H).

Workup

  1. customThe solvent was evaporated
  2. customthe resulting solid was recrystallized from methanol

Sources & evidence

ORD record
ord-b0a4ffe30b054e35adad95be4877c047
Source dataset
uspto-grants-2015_08
Patent number
US09096532B2

Reaction notes

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