Phthalimide → HCID 57826738, compound

HRID 1845360Notes

Reaction equation

HRID 1845360 reaction equation
CC([N:5]([CH:9]([CH2:19]O)[C:10]([CH3:18])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:11])[C:6](=[O:8])[O-:7])(C)C.C1(P([C:34]2[CH:39]=[CH:38]C=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:40]1(=[O:50])[NH:44][C:43](=[O:45])[C:42]2=[CH:46][CH:47]=[CH:48][CH:49]=[C:41]12.N(C(OCC)=O)=N[C:53](OCC)=O>C1COCC1.CO>[O:45]=[C:43]1[C:42]2[C:41](=[CH:49][CH:48]=[CH:47][CH:46]=2)[C:40](=[O:50])[N:44]1[CH2:19][CH:9]([NH:5][C:6](=[O:8])[O:7][C:39]([CH3:38])([CH3:34])[CH3:53])[C:10]([CH3:11])([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH3:18]

Participants

7

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 86633542HCID 86633542, compound

Product 1

HCID 57826738HCID 57826738, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1,1-dimethylethyl[1-(hydroxymethyl)-2-methyl-2-phenylpropyl]carbamate (775 mg, 2.8 mmol), triphenylphosphine (915 mg, 3.5 mmol) and phthalimide (499 mg, 3.4 mmol) in THF (15 mL) at 25° C. was added diethyl azodicarboxylate (0.54 mL, 3.4 mmol). After stirring at RT for 1 h, MeOH was added (5 mL) and the solution was adsorbed onto silica and purified via column chromatography (1% MeOH in DCM) affording the title compound (723 mg, 64%) as a white solid: LCMS (ES) m/z 409 (M+H)+.

Workup

  1. custompurified via column chromatography (1% MeOH in DCM)

Sources & evidence

ORD record
ord-6b98cb130cc544f588471971b5cb7adb
Source dataset
uspto-grants-2015_02
Patent number
US08946278B2

Reaction notes

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