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Phthalimide → HCID 66975369, compound

HRID 1022591
Notes
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Reaction equation

HRID 1022591 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:23]O)[O:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[C:25]1(=[O:35])[NH:29][C:28](=[O:30])[C:27]2=[CH:31][CH:32]=[CH:33][CH:34]=[C:26]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1.C1(C)C=CC=CC=1.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:23][N:29]3[C:25](=[O:35])[C:26]4[C:27](=[CH:31][CH:32]=[CH:33][CH:34]=4)[C:28]3=[O:30])[O:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 6809Phthalimide2×HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamate2×HCID 66975608HCID 66975608, compound

Product 1

HCID 66975369HCID 66975369, compoundYield 55.5%

Reagents, catalysts & solvents 3

HCID 962
Water
Solvent
HCID 1140TolueneSolvent2×
HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl (7RS)-7-(3,4-dichlorophenyl)-7-(hydroxymethyl)-1,4-oxazepane-4-carboxylate (2 g), phthalimide (0.86 g) and triphenylphosphine (4.17 g) in THF (40 ml) was added dropwise a solution (2.2 M, 7.2 ml) of diethyl azodicarboxylate in toluene at 0° C., and the mixture was stirred at 0° C. for 30 min, and then for 6 hr while warming to room temperature. To the reaction mixture were added phthalimide (0.43 g) and a solution (2.2 M, 3.6 mL) of diethyl azodicarboxylate in toluene, and the mixture was stirred at room temperature for 14 hr. The reaction mixture was diluted with water, and the mixture was extracted with ethyl acetate. The obtained extract was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane) and silica gel column chromatography (NH, ethyl acetate/hexane) to give the title compound (1.49 g).

Workup

  1. temperaturefor 6 hr while warming to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. extractionThe obtained extract
  4. washwas washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane) and silica gel column chromatography (NH, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-fba7353ec01b49359ab60ce6596c83a4
Source dataset
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08722662B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes