Phthalimide → HCID 18385306, compound

HRID 2298236Notes

Reaction equation

HRID 2298236 reaction equation
C(O[CH2:9][CH2:10][CH2:11][N:12]1[C:20]2[C:15](=[CH:16][C:17]([F:21])=[CH:18][CH:19]=2)[C:14]([N:22]2[C:26]([C:27]3[C:35]4[C:30](=[CH:31][CH:32]=[C:33]([F:36])[CH:34]=4)[N:29]([CH3:37])[CH:28]=3)=[N:25][NH:24][C:23]2=[O:38])=[CH:13]1)C1C=CC=CC=1.[C:39]1(=[O:49])[NH:43][C:42](=[O:44])[C:41]2=[CH:45][CH:46]=[CH:47][CH:48]=[C:40]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[F:21][C:17]1[CH:16]=[C:15]2[C:20](=[CH:19][CH:18]=1)[N:12]([CH2:11][CH2:10][CH2:9][N:43]1[C:39](=[O:49])[C:40]3[C:41](=[CH:45][CH:46]=[CH:47][CH:48]=3)[C:42]1=[O:44])[CH:13]=[C:14]2[N:22]1[C:23](=[O:38])[NH:24][N:25]=[C:26]1[C:27]1[C:35]2[C:30](=[CH:31][CH:32]=[C:33]([F:36])[CH:34]=2)[N:29]([CH3:37])[CH:28]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 18385121HCID 18385121, compound

Product 1

HCID 18385306HCID 18385306, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product from Example 1 (80 mg, 0.189 mmol) in dry THF (10 mL) was added phthalimide (42 mg, 0.28 mmol) and triphenylphosphine (74 mg, 0.28 mmol). The mixture was cooled on an ice bath and diethyl azodicarboxylate (44 μL, 0.28 mmol) was added. The reaction mixture was allowed to reach room temperature and was then stirred overnight. Concentration and silica gel chromatography (dichloromethane-methanol, 99:1/98:2/95:5) gave 73 mg (70%) of the sub-title compound.

Workup

  1. temperatureThe mixture was cooled on an ice bath
  2. customto reach room temperature
  3. concentrationConcentration and silica gel chromatography (dichloromethane-methanol, 99:1/98:2/95:5)

Sources & evidence

ORD record
ord-8710bb462bfb4d7e9eb6aaf432bbe7df
Source dataset
uspto-grants-2002_12
Patent number
US06492406B1

Reaction notes

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